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【结 构 式】

【分子编号】31234

【品名】3-(2-quinolinylmethoxy)aniline; 3-(2-quinolinylmethoxy)phenylamine

【CA登记号】

【 分 子 式 】C16H14N2O

【 分 子 量 】250.30004

【元素组成】C 76.78% H 5.64% N 11.19% O 6.39%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

Alkylation of 3-aminophenol (I) with 2-(chloromethyl)quinoline (A) in a mixture of DMSO and THF employing sodium hydride as the base affords the intermediate amine (II). This amine is reacted with trifluoromethanesulfonic anhydride in toluene employing potassium carbonate as a base to afford ritolukast.

1 Musser, J.H.; Kubrak, D.M.; Kreft, A.F. (American Home Products Corp.); Quinoline compounds as antiallergy and antithrombotic agents. EP 0232954; GB 2185741; JP 1987190159; US 4675405 .
2 Kreft, A.; Musser, J.; Daniel, W.C.; Hand, J.; RITOLUKAST < USAN >. Drugs Fut 1990, 15, 12, 1191.
3 Musser, J.H.; Kreft, A.F.; Bender, R.H.W.; Kubrak, D.M.; Carlson, R.P.; Chang, J.; Hand, J.M.; N-[(Arylmethoxy)phenyl] and N-[(arylmethoxy)naphthyl]sulfonamides. Potent orally active leukotriene D4 antagonists of novel structure. J Med Chem 1989, 32, 6, 1176.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 13162 2-(Chloromethyl)quinoline; alpha-Chloroquinaldine 4377-41-7 C10H8ClN 详情 详情
(I) 23766 3-aminophenol 591-27-5 C6H7NO 详情 详情
(II) 31234 3-(2-quinolinylmethoxy)aniline; 3-(2-quinolinylmethoxy)phenylamine C16H14N2O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

The reaction of 2-(chloromethyl)quinoline (I) with 3-nitrophenol (II) by means of Cs2CO3 in refluxing acetone gives the 3-nitrophenyl ether (III), which is reduced with H2 over Raney-Ni in ethanol to afford the 3-aminophenyl ether (IV). Finally this compound is sulfonated with trifluoromethanesulfonic anhydride and Et3N in dichloromethane.

1 Kreft, A.; Musser, J.; Substituted-[2-quinolynil(bridged)aryl] compounds: modulators of eicosanoid biosynthesis and action. Drugs Fut 1990, 15, 1, 73.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13162 2-(Chloromethyl)quinoline; alpha-Chloroquinaldine 4377-41-7 C10H8ClN 详情 详情
(II) 18076 Metanitrophenol; 3-nitrophenol 554-84-7 C6H5NO3 详情 详情
(III) 43199 3-nitrophenyl 2-quinolinylmethyl ether; 2-[(3-nitrophenoxy)methyl]quinoline C16H12N2O3 详情 详情
(IV) 31234 3-(2-quinolinylmethoxy)aniline; 3-(2-quinolinylmethoxy)phenylamine C16H14N2O 详情 详情
Extended Information