3-(4-Methoxy-2-nitrophenyl)acrylic acid methyl ester → 7-Methoxy-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

A solution of 3-(4-methoxy-2-nitro-phenyl)-acrylic acid methyl ester (4.00 g, 16.9 mmol) in MeOH (100 mL) and EtOAc (20 mL) is added a slurry of Pd/C (200 mg) in EtOH (20 mL). The suspension is hydrogenated under a pressure of 60 psi for 12 hours. The mixture is then filter through a pad of celite and the filtrate is concentrated and purified on silica gel chromatography column with 30-40-50% EtOAc/Hexanes to obtain the title product (1.30 g, 43%) and an uncyclized by-product (0.60 g).

Provenance & Evidence