Sodium hydride → 4-Hydroxy-3-(2-methylphenyl)quinolin-2(1H)-one

Participants

Reaction Steps

A mixture of methyl N-(o-tolylacetyl)anthranilate (2.8 g.) and sodium hydride (1.1 g. of a 50% w/w dispersion in mineral oil) in toluene (50ml.) was heated at 100° for 1 hr. The reaction mixture was cooled and extracted with water (2×50 ml.). The aqueous extract was acidified to pH 2. The solid which precipitated was filtered off, stirred together with hot ethanol (25 ml.), and the mixture filtered to give 4-hydroxy-3-o-tolylquinolin-2-one, m.p. over 300°.

Provenance & Evidence