N-(4-bromo-2-methylphenyl)-3-oxobutanamide → 6-Bromo-4,8-dimethylquinolin-2(1H)-one

Participants

Reaction Steps

N-[4-Bromo-2-methylphenyl]-acetoacetamide (18 g) was heated for 5 hours with stirring in 98% sulphuric acid (50 cm3) at 100°. The cooled mixture was then poured onto ice (200 g), the solid was filtered off and dried in vacuo at 100° for 2 hours to give the crude product (15.0 g). A small portion (1.5 g) of this material was recrystallised from ethyl acetate/methanol to afford 6-bromo-4,8-dimethyl-2-(1H)-quinolone, m.p. >300° (1.1 g).

Provenance & Evidence