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-chloroperbenzoic acid (85%, 2.3 g) and methanol (40 ml) was stirred for 2 hours under reflux. The solvent in the reaction mixture was evaporated under reduced pressure, and the residue was poured into chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (=6/4, v/v) gave ethyl 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate 1-oxide (2.0 g, 65%) which was then recrystallized from acetone-isopropyl ether.

Provenance & Evidence