m-Chloroperbenzoic acid → Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide

Participants

Reaction Steps

A mixture of ethyl 2-chloromethyl-6,7-dimethoxy-4- (3,4-dimethoxyphenyl)quinoline-3-carboxylate (3.0 g), m-chloroperoxybenzoic acid (85%, 2.3 g) and methanol (40 ml) was stirred under reflux for 2 hours. The solvent of the reaction mixture was distilled off under reduced pressure. The residue was poured into chloroform. The chloroform layer was washed with water and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform/ethyl acetate (6:4, v/v), ethyl 2-chloromethyl-6,7-dimethoxy-4-(3,4- dimethoxyphenyl)quinoline-3-carboxylate 1-oxide (2.0 g, 65%) was obtained and recrystallized from acetone/isopropyl ether.

Provenance & Evidence