Category: 18436-73-2

Synthetic Route of C10H8ClN. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Study of aminoquinolines. XIV: Long-chain 4-alkylaminoquinolines with potential amebicide activity. Part 2: Effect of the position of nuclear alkyl groups.

Alkylaminoquinolines I (n = 7-17; R = 2-Me, 2-Ph, H, 3-Me; R1 = H, S-Me, 6-Me, 7-Me, 8-Me, 8-Et, 8-CHMe2) were prepared by aminating 4-chloroquinolines. The amebicidal activity of I was maximum when n = 7-9. Methylation of the ring had little effect on amebicidal activity. Some of the chloroquinolines were prepared by treating anilines with EtOCH:C(CO2Et)2 or AcCH2CO2Et, cyclizing, decarboxylating the quinolinecarboxylates, and chlorinating the quinolinol.

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Quality Control of 4-Chloro-8-methylquinoline. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Synthesis and photochemistry of two quinoline analogs of the perimidinespirohexadienone family of photochromes. Author is Moerdyk, Jonathan P.; Speelman, Amy L.; Kuper, Kenneth E.; Heiberger, Brian R.; Ter Louw, Ryan P.; Zeller, Daniel J.; Radler, Andrew J.; Gillmore, Jason G..

The authors report the detailed synthesis and photochem. of two analogs (specifically 3,5-di-tert-butyl-7′-methyl- and 3,5-di-tert-butyl-7′,9′-dimethyl-1′,3′-dihydrospirocyclohexa[2,5]diene-1,2′-pyrido[4,3,2-de]quinazolin-4-one) of the perimidinespirohexadienone (3,5-di-tert-butyl-1′,3′-dihydrospirocyclohexa[2,5]diene-1,2′-perimidin-4-one) family of photochromes in which the naphthalene moiety of the parent is replaced by a quinoline, and compare them to the parent compound Molar absorptivities of both the short wavelength spirocyclic isomer (SW) and long wavelength quinonimine isomer (LW) of each were determined by a combination of proton NMR and UV-vis spectroscopy in solvents of varying polarity. Quantum yield measurements for photoisomerization of SW to LW are reported in those same solvents, with qual. extrapolation to addnl. solvents. The position and rate of the thermal equilibrium reverting LW to SW is estimated for these compounds The 9′-Me in SW (6-Me in LW) is found to be essential for complete reversion of LW to SW in the dark. Finally one-dimensional NOE NMR spectroscopy was used to conclusively determine the structure of LW for the quinoline analogs as the 4-(5-aminoquinolin-4-ylimino)-2,6-di-tert-butylcyclohexa-2,5-dienone resulting from opening toward the quinoline nitrogen, rather than the 4-(4-aminoquinolin-5-ylimino) structure that would result from spirocyclic ring opening away from the quinoline nitrogen which had been initially proposed by V.I Minkin et al. (1999) for very similar compounds

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Denny, William A.; Atwell, Graham J.; Roberts, Peter B.; Anderson, Robert F.; Boyd, Maruta; Lock, Colin J. L.; Wilson, William R. published an article about the compound: 4-Chloro-8-methylquinoline( cas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1 ).Computed Properties of C10H8ClN. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:18436-73-2) through the article.

A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines, e.g., I [Rn = H, 3-, 5-, 6-, 7-, 8-NO2, 2,5-Me(O2N), 3,5-Me(O2N), 6,5-Me(O2N), 8,5-Me(O2N), 7,8-Me(O2N), 7,6-Me(O2N), 2,3-Me(O2N)], has been synthesized and evaluated as hypoxia-selective cytotoxins and as radiosensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogs were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pKa. Two compounds of lower reduction potential, the 3- and 8-Me analogs, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest in vitro therapeutic indexes of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the maximum tolerated dose.

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Tricyclic heteroaromatic ring systems. II. A convenient synthesis of 1H-pyrrolo[3,2-c]quinolines.Application In Synthesis of 4-Chloro-8-methylquinoline.

Quinol-4-yl hydrazones I (R = H, Me, Et; R1 = Me, Ph, Et; RR1 = (CH2)n, n = 3, 4; R2 = H, Me; R3 = H, 6-, 7-, 8-Cl, 6-, 7-, 8-Me, 6-, 7-, 8-MeO) on heating in high boiling solvents undergo cyclizations to give 1H-pyrrolo[3,2-c]quinolines II in good yields. Some of these I were alkylated to provide their N-alkyl derivatives

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Ru(II)/Rh(III)-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Activation: Selective Linear Alkylation of 8-Methylquinolines and Ketoximes with Olefins, the main research direction is alkylquinoline alkylsantonin oxime regioselective preparation; ruthenium rhodium catalyst regioselective alkylation methylquinoline acrylate styrene alkene; regioselective alkylation methylquinoline santonin oxime ether alkene ruthenium catalyst; rhodium catalyst regioselective alkylation methylquinoline santonin oxime ether alkene; mechanism kinetic isotope effect regioselective alkylation methylquinoline acrylate.Recommanded Product: 18436-73-2.

In the presence of either [RuCl2(p-cymene)]2 or [Cp*RhCl2]2 and AgSbF6, 8-methylquinolines underwent regioselective alkylation with acrylates, styrenes, and other alkenes mediated by pivalic acid in hexafluoroisopropanol to yield 8-alkylquinolines with linear alkyl substituents. The mechanism of the reaction was studied using deuterium labeling, kinetic isotope effect, and competition studies; the reaction may proceed through a five-membered metallacycle intermediate. Under similar conditions, an O-methyloxime derivative of (-)-santonin underwent regioselective alkylation with Et acrylate and acrylonitrile.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Dalton Transactions called Well-defined palladium(II) complexes for ligand-enabled C(sp3)-alkynylation, Author is Landge, Vinod G.; Sahoo, Manoj K.; Midya, Siba P.; Jaiswal, Garima; Balaraman, Ekambaram, which mentions a compound: 18436-73-2, SMILESS is CC1=C2N=CC=C(Cl)C2=CC=C1, Molecular C10H8ClN, Reference of 4-Chloro-8-methylquinoline.

The first example of ligand-enabled C(sp3)-alkynylation of 8-methylquinoline is reported. The reaction is catalyzed by well-defined Pd(II) complexes. The present C(sp3)-alkynylation has a broad substrate scope as well as functional group tolerance and proceeds efficiently under mild conditions.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins, published in 1992-12-25, which mentions a compound: 18436-73-2, Name is 4-Chloro-8-methylquinoline, Molecular C10H8ClN, Synthetic Route of C10H8ClN.

A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines, e.g., I [Rn = H, 3-, 5-, 6-, 7-, 8-NO2, 2,5-Me(O2N), 3,5-Me(O2N), 6,5-Me(O2N), 8,5-Me(O2N), 7,8-Me(O2N), 7,6-Me(O2N), 2,3-Me(O2N)], has been synthesized and evaluated as hypoxia-selective cytotoxins and as radiosensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogs were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pKa. Two compounds of lower reduction potential, the 3- and 8-Me analogs, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest in vitro therapeutic indexes of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the maximum tolerated dose.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aminoalkylphenols as antimalarials. II. (Heterocyclic amino)-α-amino-ο-cresols. The synthesis of camoquin》. Authors are Burckhalter, J. H.; Tendick, F. H.; Jones, Eldon M.; Jones, Patricia A.; Holcomb, W. F.; Rawlins, A. L..The article about the compound:4-Chloro-8-methylquinolinecas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1).Recommanded Product: 4-Chloro-8-methylquinoline. Through the article, more information about this compound (cas:18436-73-2) is conveyed.

In view of the high antimalarial activity of certain substituted α-amino-ο-cresols, earlier work (C.A. 41, 414d) has been extended to analogs containing heterocyclic nuclei. This reports the preparation of a group of 122 (heterocyclic amino)-α-amino-ο-cresols and a related group of 12 (heterocyclic amino)benzylamines, as well as the new intermediates used therein. This work has resulted in the preparation of a promising antimalarial (SN 10,751) named camoquin, as well as other compounds which are the most active 4-aminoquinoline derivatives heretofore reported in trophozoite-induced Plasmodium gallinaceum infection in the chick. Catalytic reduction of the appropriate nitrophenol in the presence of Ac2O gave these 4-acetamidophenols: 2-Cl, m. 144°, 55% yield; 2-Ph, m. 160°, 60%; and 2-acetamidophenols: 4-Cl, m. 186°, 52%; 4-Ph, m. 165°, 89%; and 4-tert-Bu, m. 170°, 79%. 2-Allyl-4-acetamidophenol, m. 93-4°, was obtained in 83% yield from the rearrangement of 4-CH2:CHCH2OC6H4NHAc. The Mannich reaction on the substituted acetamidophenols gave these 4-acetamido-α-substituted-ο-cresols: diethylamino (I), m. 135°, 82%; dibutylamino, m. 73°, 87% (picrate, m. 183-5°); dibenzylamino, m. 230°, 75%; (2-methyl-1-piperidyl) (HCl.H2O, m. 175°, 65%); 4-morpholinyl, m. 133°, 27%; [methyl(2-hydroxyethyl)amino] (HCl, m. 198°, 50%); (2-butylamino), m. 156°, 37%; (2-hydroxyethylamino) (HCl, m. 230°, 31%); the 6-allyl derivative of I, m. 86°, 58%: the 5-acetamido isomer of I (HCl, m. 210°, 33%); and these 6-acetamido-α-diethylamino-4-substituted-ο-cresols: Cl (HCl, m. 212°, 66%); tert-Bu (HCl, m. 158°, 53%); and Ph (HCl, m. 183°). Acid hydrolysis of the appropriate 4-acetamido compound gave these 4-amino-α-substituted-ο-cresols (di-HCl salts) (all m. with decomposition); diethylamino, SN 12,458, m. 218-20°, 96%; 1-piperidyl, m. 153-5°, 91%; and 4-morpholinyl, m. 259-60°, 45%. The Mannich reaction on 4-nitrophenol (A) and the reaction of the amine on 2-(chloromethyl)-4-nitrophenol (B) were used to prepare these α-substituted-4-nitro-ο-cresol HCl salts (all m. with decomposition): diethylamino, A, m. 224°, 40%; diisopropylamino, B, m. 193°, 19%; dibutylamino, B, m. 176°, 75%; diisobutylamino (free base), B, m. 113°, 43%; diisoamylamino, B, m. 132°, 32%; isopropylamino, B, m. 238°, 38%; isobutylamino, B, m. 247°, 29%; tertbutylamino, B, m. 275°, 20%; 1-piperidyl, A, m. 260°, 68%; and α-diethylamino-4-nitro-6-phenyl-ο-cresol, A, m. 125°, 21%; and 4-tert-butyl-α-diethylamino-6-nitro-ο-cresol, A, m. 103°, 50%. The method of Price and Roberts (C.A. 40, 5739.5) was used to prepare these substituted 4-chloroquinolines: 6-Me, m. 55°, 50%; 6-anilino, m. 148°, 6%; 7-EtO, m. 76°, 53%; 7-hexyloxy, a high-boiling liquid, 41%; 8-Me, m. 99°, 71%; 5,7-di-Me, m. 59°, 51%; 5,8-di-Me, m. 51°, 59%; 5-chloro-8-methoxy, m. 127°, 6%; 5-methyl-8-methoxy, m. 78°, 45%; 6,8-di-Me, m. 90°, 82%; and 6,7,8-trichloro, m. 156°, 39%. The (heterocyclic amino)-α-alkylamino-ο-cresols were prepared by minor variations of the general procedure of heating the chloroheterocycle with the amino-α-alkylamino-ο-cresols in aqueous or alc. solution on the steam bath. The latter were obtained either by acid hydrolysis of the acetamido derivatives or by catalytic reduction of the nitro derivatives and were usually condensed without isolation. The products are isolated either as the free bases or HCl salts. All the quinine equivalents (Q) reported here are based on the B4 test using P. gallinaceum in the chick. Nearly all the HCl salts m. with decomposition and are colored yellow to orange. 4-(4-Quinolylamino)-α-diethylamino-ο-cresol (II) di-HCl, SN 12,452, m. above 300°, was obtained in 48% yield and had a quinine equivalent of 3 (designated hereafter in the form Q 3). Analogs of II, substituted on the quinoline nucleus: 2-Cl (2HCl, SN 11,986, m. 248°, 30%, Q <0.07); 3-Ph, SN 11,631, m. 155°, 31%, Q 0.4; 6-MeO (2HCl, SN 10,274, m. 270°, 75%, Q 8); 6-Cl (HCl.0.5H2O, SN 11,597, m. 220°, 60%, Q 3.0); 6-Me, SN 11,559, m. 172° (2HCl, m. 238°, 56%, Q 4); 6-anilino (2HCl.H2O, SN 12,361, m. 196°, 63%, Q 0.2); 6-dimethylamino (3HCl.0.5H2O, SN 11,984, m. 235°, 73%, Q 2.5); 6-nitro (2HCl.1.5H2O, m. 210°, 63%, Q 0.8); 7-MeO (2HCl.0.5H2O, SN 11,554, m. 210°, 43%, Q 7); 7-EtO (2HCl.2H2O, SN 11,281, m. 136°, 44%, Q 7); (7-hexyloxy, SN 11,634, m. 153°, 35%, Q 0.5; Q 7); 7-Me (2HCl, SN 12,699, m. 245°, 93%, Q 9); 7-Cl (camoquin) SN 10,751, m. 208°, 86%, Q 25 (2HCl.0.5H2O, m. 243°); 2HCl.H2O, m. 183°; (2HCl.2H2O, m. 160°, 90%); 8-Cl, SN 11,551, m. 212° (2HCl.0.5H2O, m. 253°, 79%, Q 0.5); 8-MeO (2HCl.1.5H2O, SN 11,594, m. 241°, 50%, Q 0.8); 8-Me (2HCl.H2O, SN 11,601, m. 253°, 66%, Q 0.7); 5-chloro-3-Me (2HCl, SN 11,985, m. 258°, 48%, Q 0.3); 5,7-di-Cl (2HCl, SN 12,700, m. 200°, 65%, Q 3); 5,7-di-Me (2HCl, SN 11,561, m. 242°, 67%, Q 10); 5,8-di-Cl (2HCl.H2O, SN 11,596, m. 235°, 60%, Q 0.25); 5,8-di-Me (2HCl, SN 11,560, m. 249°, 80%, Q 0.6); 5-chloro-8-methoxy [2HCl, SN 12,162,(incorrectly given as 12,161 in original), m. 231°, 80%, Q 0.4]; 6-methoxy-2-Me (2HCl, SN 9223, m. 278°, 45%, Q 1.2); 6-methoxy-2-Ph (2HCl.1.75H2O, SN 11,592, m. 198°, 61%, Q 0.25); 6,7-di-Cl (2HCl, SN 12,161, m. 257°, 71.5%, Q 5); 6,7-di-MeO (2HCl, SN 13,395, m. 258°, 68%, Q 2.5); 6,7-di-Me, SN 11,990, m. 215°, 49%, Q 6; 6,8-di-Me (2HCl.H2O, SN 11,558, m. 264°, 54%, Q 0.6); 7-chloro-2-Ph (2HCl, SN 11,232, m. 260°, 41%, Q 0.3); 7-chloro-3-Ph, SN 12,228, m. 165°, Q 1; 7-chloro-3-Me (2HCl, SN 10,492, m. 260°, 64%, Q 6); 8-methoxy-5-Me (2HCl, SN 11,632, m. 210°, 90%, Q 0.6); 6,7,8-tri-Cl (2HCl, SN 11,633, m. 277°, 40%, Q <0.3); and 6-HO (2HCl, SN 11,563, m. 262°, 64%, Q 0.2) (prepared by HBr demethylation of the 6-MeO derivative). 4-(6-Methoxy-4-quinolylamino)-α-dibutylamino-ο-cresol (III) (2HCl.1.25H2O, m. 193°, 10%, Q 9); the (7-chloro-3-methyl-4-quinolylamino) analog of III (2HCl.1.5H2O, m. 177°, 43%, Q 10). 4-(6-Methoxy-4-quinolylamino)-α-1-piperidyl-ο-cresol (IV) (2HCl.0.5H2O, SN 12,038, m. 270°, 80%, Q 8); analogs of IV: (6,7-dimethoxy-4-quinolylamino) (2HCl, SN 13,413, m. 230°, 40%, Q 4); (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,360, m. 270°, 47%, Q 2); (6-methyl-4-quinolylamino) (2HCl, SN 12,456, m. 240°, 41%, Q 2.5). 4-(6-Methoxy-4-quinolylamino)-α-4-morpholinyl-ο-cresol (V) (2HCl, SN 11,989, m. 265°, 57%, Q 1); analogs of V: (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,362, m. 242°, 33%, Q 0.15); (6-methyl-4-quinolylamino), SN 12,457, m. 239°, 50%, Q 0.8. 5-(7-Chloro-4-quinolylamino)-α-diethylamino-ο-cresol, SN 13,730, m. 173°, Q 9; 6-(7-chloro-4-quinolylamino)-α-diethylamino-4-(diethylaminomethyl)-ο-cresol-1.5H2O, m. 145°, Q 5; 4-chloro-α-diethylamino-6-(6-methoxy-4-quinolylamino)-ο-cresol (2HCl, SN 12,885, m 205°, 50%, Q 0.5). 6-Chloro-4-(7-chloro-4-quinolylamino)-α-diethylamino-ο-cresol (VI), SN 13,729, m. 225°, Q 12; analogs of VI: 6-Ph (0.5H2O, m. 235°, 25%); 6-allyl, SN 11,991, m. 148°, 44%, Q 10; 6-allyl-α-1-piperidyl, SN 12,697, m. 190°, 32%, Q 4; 6-allyl-α-diallylamino, SN 13,394, m. 131°, 25%, Q 0.7. 6-Allyl-α-diethylamino-4-(6-methoxy-4-quinolylamino)-ο-cresol, SN 12,039, m. 161°, 33%, Q 7. Variations of the alkylamino group on the cresol portion of camoquin were studied: α-amino-4-(7-chloro-4-quinolylamino)-ο-cresol (VII) (2HCl.0.5H2O, SN 1603, m. 325°, 80%, Q 6); analogs of VII (substituents on the α-amino group): benzoyl (HCl, SN. 11,557, m. 289°, 80%, Q 0.15); Et (2HCl, m. 280°, Q 40, 4% conversion, prepared by the Mannich reaction of EtNH2, (HCHO)x, and 7-chloro-4-(4-hydroxyanilino)quinoline (HCl, m. above 320°, 94%)); Pr(2HCl.0.5H2O, m. 244°, 24%, Q 30); iso-Pr (2HCl, m. 287° 50%, Q 40); Bu (2HCl, m. 254°, 6%, Q 30); sec-Bu (2HCl.H2O, m. 252°, 3%, Q 50); iso-Bu (2HCl, m. 256°, 65%, Q 75); tert-Bu (2HCl, m. 285°, 36%, Q 40); Am (2HCl, m. 266°, 15%, Q 50); (1-methylbutyl 2HCl, m. 231°, 22%, Q 40); iso-Am (2HCl, m. 279°, 20%, Q 50); hexyl (2HCl, m. 280°, 56%, Q 25); (2-ethylbutyl (2HCl, m. 263°, 15%, Q 50)); heptyl (2HCl, m. 278°, 29%, Q 15); octyl, m. 150°, 15%, Q 2.5; allyl (2HCl, m. 257°, 3%, Q 20); 1-methylallyl (2HCl.1.75H2O, m. 95°); cyclohexyl (2HCl.0.25H2O, m. 252°, 30%, Q 30); 2-hydroxyethyl (2HCl.H2O, m. 182°, 15%, Q 3); 2-methoxyethyl (2HCl, m. 271°, Q 25); benzyl (2HCl, m. 270°, Q 16); (α-methylphenethyl) (2HCl.0.25H2O, m. 243°, 31%, Q 25); di-Me (2HCl, m. 290°, 85%, Q 6); N-ethyl-N-butyl(2HCl, m. 240°, 65%, Q 30); di-Pr, SN 13,835, m. 181°, 11%, Q 25; di-Bu, SN 14,105, m. 164°, 20%, Q 35; diiso-Bu (0.5H2O, m. 166°, 38%); diiso-Am (0.5H2O, m. 135°); dihexyl (2HCl, m. 220°, 40%, Q 0.5); diheptyl (2HCl, m. 203°, 52%, Q 1); dioctyl (2HCl, m. 192°, 46%, Q 0.2); bis(2-ethylhexyl) (2HCl.H2O, m. 154°, 1%, Q 3); methyl(2-hydroxyethyl) (2HCl, SN 12,363, m. 250°, 63%, Q 3); butyl(2-hydroxyethyl), SN 14,824, m. 149°, 22%, Q 12; bis(2-hydroxyethyl), m. 193°, 25%, Q 0.6; dibenzyl (2HCl, m. 235°, 74%, Q 2.5); N-methyl-N-Ph (H2O, m. 140°, 39%, Q 0.07); N-ethyl-N-Ph, m. 131°, 54%, Q <0.05. Further analogs of VII: α-1-piperidyl (2HCl.2.5H2O, SN 11,636, m. 302°, 77.5%, Q 25); α-(2-methyl-1-piperidyl) (2HCl, SN 12,357, m. 288°, 66%, Q 20); α-4-morpholinyl (2HCl, SN 11,987, m. 292°, 60-5%, Q 4). Compounds containing heterocyclic nuclei other than the 4-quinolyl include the following 4-(heterocyclic amino)-α-diethylamino-ο-cresols: 9-acridyl (2HCl, SN 12,356, m. 265°, 45%, Q 1.5); (3-chloro-9-acridyl) (2HCl, SN 12,355, m. 267°, 52%, Q 3); (4-methoxy-9-acridyl) (2HCl, SN 12,164, m. 245°, 50%, Q 0.15); (3-chloro-5-methyl-9-acridyl) (2HCl, SN 11,988, m. 275°, 40%, Q 0.25); 2-quinolyl (2HCl, SN 9559, m. 230°, 48%, Q 0.12); (6-methoxy-2-quinolyl) (2HCl, SN 11,537, m. 237°, 20.5%, Q 0.7); (5-nitro-2-quinolyl) (2HCl, SN 9307, m. 245°, 33%, Q <0.07); (2-amino-4-pyrimidyl) (2HCl, SN 9591, m. 258°, 41%, Q 1.1); [2-(1-piperidyl)-4-pyrimidyl], SN 10,177, m. 156°, 31%, Q 0.4; (2-amino-6-methyl-4-pyrimidyl) (2HCl, m. 245°, 55%); (4-methoxy-2-benzothiazolyl) (2HCl, SN 11,189, m. 163°, 47%, Q <0.07); (6-chloro-2-methoxy-9-acridyl) (VIII), SN 8617, m. 175°, 50% (H2O, m. 117°; 2HCl, m. 280°, 76%, Q 4; 2HCl.2H2O, m. 180°); analogs of VIII: α-(ethylbutylamino) (2HCl, m. 252°, 36%, Q 5); α-dibutylamino (2HCl, SN 11,599, m. 246°, 69%, Q 2.5); α-diallylamino, SN 13,163, m. 158°, 16%, Q 0.5; α-dihexylamino (2HCl, m. 254°, 23%, Q 0.4); α-dioctylamino (2HCl, m. 285°, 20%, Q <0.06); α-1-piperidylamino (2HCl, SN 11,536, m. 287°, Q 0.6); α-hexylamino (2HCl.H2O, m. 226°, 7%, Q 1); α-(2-hydroxyethylamino) (2HCl.H2O, SN 11,233, m. 284°, 90%, Q 0.2); α-benzamido (HCl.0.5H2O, SN 11,589, m. 294°, 95%, Q <0.04). 5-(6-Chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (2HCl.0.5H2O, SN 9614, m. 237°, 50%, Q 1); 4-tert-butyl-6-(6-chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (IX) (2HCl, SN 11,544, m. 271°, 98%, Q 0.6); 4-Ph analog of IX (2HCl, SN 11,553, m. 274°, 84%, Q 0.5); 4-diethylaminomethyl analog of IX (3HCl.H2O, SN 11,550, m. 257°, 73%, Q 2); 6-allyl-4-(6-chloro-2-methoxy-9-acridylamino)-α-diethylaminο-ο-cresol (X) (2HCl, SN 11,234, m. 233°, 65%, Q 3); α-diallylamino analog of X (2HCl.H2O, SN 13,399, m. 188°, 12%, Q 0.3); and α-1-piperidyl analog of X, SN 12,701, m. 164°, 44%, Q 2. A series of nitrobenzylamines was prepared by condensation of the nitrobenzyl chloride with the amine in absolute EtOH. During the course of this work, 2-(chloromethyl)-4-nitrophenetole,m. 72-5°, was obtained in 75% yield from the chloromethylation of 4-nitrophenetole. The nitrobenzylamines were reduced catalytically in absolute EtOH and the resulting aminobenzylamines without isolation were condensed with the chloroheterocycle. Thus were obtained: N,N-diethyl-3-nitrobenzylamine, b6 145-8°, 60%; 4-nitro isomer (XI) (HCl, m. 162°, 45%); analogs of XI: N,N-di-Pr (HCl, m. 138°, 68%); N-monoisopropyl (HCl, m. 232°, 82%); N-monoisobutyl (HCl, m. 214°, 64%). N,N-Diethyl-5-nitro-2-methoxybenzylamine (XII) (HCl, m. 178°, 72%); analogs of XII: N-monoisobutyl (HCl, m. 176°, 63%); N-monoamyl (HCl salt could not be separated from an impurity of AmNH2.HCl). N,N-Diethyl-5-nitro-2-ethoxybenzylamine (HCl, m. 182°, 56%). 3-(7-Chloro-4-quinolylamino)-N,N-diethylbenzylamine (2HCl.2H2O, SN 11,590, m. 128° (all these HCl salts m. with decomposition), 85%, Q 1); 4-(7-chloro-4-quinolylamino)-N,N-diethylbenzylamine (XIII) (2HCl, SN 12,455, m. 261°, Q 4); N,N-di-Pr analog of XIII (2HCl, m. 255°, 60%, Q 4); the N-monoisopropyl analog of XIII (2HCl salt, m. 303°, 23%, Q 10); N-monoisobutyl analog of XIII (2HCl.H2O, m. 288°, 76%); 5-(7-chloro-4-quinolylamino)-N,N-diethyl-2-methoxybenzylamine (XIV), m. 203°, 64%, Q 25; N-monoisobutyl analog of XIV (2HCl.0.25H2O, m. 194°, 76%, Q 17); N-monoamyl analog of XIV (2HCl, m. 288°, 42%, Q 15); 2-ethoxy analog of XIV (2HCl.2H2O, m. 247°, 73%, Q 8); 3-(6-chloro-2-methoxy-9-acridylamino)-N,N-diethylbenzylamine (XV) (2HCl.0.75H2O, SN 10,984, m. 278°, 55%, Q 0.5); the 4-substituted benzyl isomer of XV (2HCl.0.5H2O, SN 10,028, m. 260°, 92%, Q 0.4); and 5-(6-chloro-2-methoxy-9-acridylamino)-2-methoxy-N,N-diethylbenzylamine (2HCl.0.5H2O, m. 212°, 67%, Q 3). 6-Chloro-9-(4-hydroxyanilino)-2-methoxyacridine, m. 266° (decomposition) (HCl, orange, m. above 300°, prepared in 98% yield from p-NH2C6H4OH and 6,9-dichloro-2-methoxyacridine on the steam bath), failed to undergo the usual Mannich reaction. Failure of this reaction led to the development of the method of synthesis used for all of the heterocyclic derivatives reported in this paper. I hope my short article helps more people learn about this compound(4-Chloro-8-methylquinoline)Recommanded Product: 4-Chloro-8-methylquinoline. Apart from the compound(18436-73-2), you can read my other articles to know other related compounds.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application In Synthesis of 4-Chloro-8-methylquinoline. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about A mild and efficient method for the preparation of 3-(2′-aminoaryl)pyrazoles from 4-chloroquinolines. Author is Borges, Julio C.; de Oliveira, Cesar D.; da Silva Pinheiro, Luiz C.; Marra, Roberta K. F.; Khan, Misbahul Ain; Wardell, James L.; Wardell, Solange M. S. V.; Bernardino, Alice M. R..

The authors described a mild and efficient method for the formation of 3-(2′-aminoaryl)pyrazoles in excellent yields from reactions of 4-chloroquinolines with hydrazine. These heterocyclic ring opening reactions occur under much milder conditions then previously described. The structures of the compounds were determined by spectral data and confirmed by x-ray diffraction anal. of 3-(2′-amino-3′-methylphenyl)pyrazole [monoclinic, C2, a 25.9750(3), b 9.5820(6), c 7.8299(7) Å, β 107.541(3)°, V 1858.2(2) Å3, Z 8].

I hope my short article helps more people learn about this compound(4-Chloro-8-methylquinoline)Application In Synthesis of 4-Chloro-8-methylquinoline. Apart from the compound(18436-73-2), you can read my other articles to know other related compounds.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Zhu, You-Quan; He, Jing-Li; Niu, Yun-Xia; Han, Ting-Feng; Zhu, Kun published the article 《Rapid Microwave-Assisted, Solvent-Free Approach to Functionalization of 8-Methylquinolines via Rh-Catalyzed C(sp3)-H Activation》. Keywords: aryl quinolinyl acetamide preparation; methylquinoline phenyl isocyanate microwave assisted CH activation; quinolinyl methyl benzamide preparation; phenyl dioxazolone methylquinoline microwave assisted CH activation.They researched the compound: 4-Chloro-8-methylquinoline( cas:18436-73-2 ).Name: 4-Chloro-8-methylquinoline. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:18436-73-2) here.

A microwave-assisted synthesis of aryl (quinolinyl)acetamide derivatives I [R1 = H, 6-Cl, 4-Br, etc.; R2 = 3-Me, 4-F, 4-Cl, etc.] and quinolinyl (methyl)benzamide II via Rh-catalyzed C(sp3)-H activation of 8-methylquinoline under solvent-free condition was reported. In comparison with traditional method, this reaction proceeded more efficiently with excellent yield, a broad range substrate scope and good functional group tolerance.

From this literature《Rapid Microwave-Assisted, Solvent-Free Approach to Functionalization of 8-Methylquinolines via Rh-Catalyzed C(sp3)-H Activation》,we know some information about this compound(18436-73-2)Name: 4-Chloro-8-methylquinoline, but this is not all information, there are many literatures related to this compound(18436-73-2).

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia