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【结 构 式】

【分子编号】21104

【品名】2-chloro-4-phenylquinoline

【CA登记号】

【 分 子 式 】C15H10ClN

【 分 子 量 】239.70384

【元素组成】C 75.16% H 4.2% Cl 14.79% N 5.84%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

This compound can be prepared by two related ways: 1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II), which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III). The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV), which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V). The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI), which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII). Finally, this compound is condensed with N-ethylpiperazine (VIII) at 130 C. 2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X), which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.

1 Uno, H.; Nagai, Y.; Karasawa, T.; Furukawa, K. (Dainippon Pharm. Co.; Ltd.); 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its salts with acids, process for their preparation and their use as antidepressant agents. DE 2912414 .
2 Uno, H.; Nagai, Y.; Hino, K.; Kawashima, K.; Oka, M.; Matsumoto, J.; A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines. Chem Pharm Bull 1989, 37, 1, 110.
3 Prous, J.; Castaner, J.; AD-2646. Drugs Fut 1989, 14, 8, 735.
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) 20951 2-nitrobenzoic acid;o-Nitrobenzoic acid 552-16-9 C7H5NO4 详情 详情
(II) 21099 o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride 610-14-0 C7H4ClNO3 详情 详情
(III) 21100 (2-nitrophenyl)(phenyl)methanone 2243-79-0 C13H9NO3 详情 详情
(IV) 21101 (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone 2835-77-0 C13H11NO 详情 详情
(V) 21102 N-(2-benzoylphenyl)acetamide 85-99-4 C15H13NO2 详情 详情
(VI) 21103 4-phenyl-2(1H)-quinolinone C15H11NO 详情 详情
(VII) 21104 2-chloro-4-phenylquinoline C15H10ClN 详情 详情
(VIII) 14213 N-Ethylpiperazine; 1-Ethylpiperazine 5308-25-8 C6H14N2 详情 详情
(IX) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
(X) 21107 4-phenyl-2-(1-piperazinyl)quinoline C19H19N3 详情 详情
Extended Information