Water → 4-Methoxy-3-(2-methylphenyl)quinolin-2(1H)-one

Participants

Reaction Steps

A mixture of 2,4-dichloro-3-o-tolylquinoline (3 g.) and sodium methoxide (1.9 g.) in dimethylformamide (30 ml.) was heated at 60° for 6 hr. The mixture was cooled and poured into water (500 ml.), and the mixture was extracted with ethyl acetate (2×100 ml.). The ethyl acetate extract was washed with water (2×50 ml.) and then dried (MgSO4). The solvent was evaporated and the residue (containing 2,4-dimethoxy-3-o-tolylquinoline) was used without further purification. A mixture of said residue (2.6 g.) and 2M-hydrochloric acid (50 ml.) was heated at 100° for 2 hr. The mixture was cooled and filtered. The solid residue was crystallised from ethyl acetate-petroleum ether (b.p. 60°-80°) to give 4-methoxy-3-o-tolylquinolin-2-one, m.p. 215°.

Provenance & Evidence