Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate → 5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

Participants

Reaction Steps

A suspension of methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate (5.0 g, 14.07 mmol) in ethanol (100 mL) is hydrogenated with Raney nickel (3 g) at ambient temperature and 4 bar hydrogen pressure. After 6 hours, more Raney nickel (2 g) is added and the mixture is hydrogenated for a further 2 hours. The catalyst is separated off and the filtrate is combined with 2 M aqueous hydrochloric acid (15 mL). The product that crystallizes out is filtered off and dried. Yield: 1.0 g (24%); mass spectroscopy: [M+H]+=296.

Provenance & Evidence