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159782-19-1

2-(3-METHOXYPHENYL)QUINOLINE-4-CARBOXYLIC ACID synthesis

2synthesis methods
-

Yield:159782-19-1 43%

Reaction Conditions:

with potassium hydroxide in ethanol;lithium hydroxide monohydrate at 80;

Steps:

5.11 General procedure for preparation of 2-arylquinoline-4-carboxylic acid (11a-h)

General procedure: To a stirring mixtures of indoline-2,3-dione (3.1g, 0.02mol) in 33% potassium hydroxide solution (10mL), various substituted acetophenone (1.1equiv) in ethanol (30mL) was dropped slowly. The resulting reaction mixture was heated to 80°C for 24-72h, and monitored by TLC. The solvent was concentrated in vacuum and the residue was dissolved by water (100mL), which was extracted with diethyl ether (100mL×3), and the aqueous layer was acidified with glacial acetic acid to pH 5. The resulting precipitate was filtered, dried, and recrystallized with ethanol to yield a series of 2-arylquinoline-4-carboxylic acids 11a-h.

References:

Li, Sai;Huang, Qiang;Liu, Yajing;Zhang, Xiaolong;Liu, Shuang;He, Chao;Gong, Ping [European Journal of Medicinal Chemistry,2013,vol. 64,p. 62 - 73]