5-Nitro-1,2-dihydroquinolin-2-one → 5-Amino-1,2-dihydroquinolin-2-one

Participants

Reaction Steps

A solution of 2.1 g (11 mmol) of 5-nitro-1H-quinolin-2-one (Chem. Pharm. Bull. 1981, 29, 651) in 40 ml of AcOH is hydrogenated with 210 mg of 10% Pd/C in the presence of hydrogen for 24 h with vigorous stirring. The catalyst is filtered off and the mixture is evaporated. The residue is subjected to flash chromatography over SiO2 with a gradient of pure CH2Cl2 to CH2Cl2-MeOH 99-1. After evaporation, 1.67 g (yield 97%) of yellow crystals are obtained. 1H NMR (DMSO): 11.38 (s, 1H), 8.08 (d, 1H, J=8 Hz), 7.10 (t, 1H, J=7.6 Hz), 6.44 (d, 1H, J=8 Hz), 6.33 (d, 1H, J=8 Hz), 6.26 (d, 1H, J=10 Hz), 5.85 (s, 2H).

Provenance & Evidence