8-Methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one → 7-Amino-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one

Participants

Reaction Steps

To a solution of 8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (360 mg, 1.5 mmol) in methanol (30 mL) was added palladium 10% wt on Carbon (50% wet; 50 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) for 30 minutes. Filtration through Celite and evaporation of the solvent provided 7-amino-8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (300 mg, 95%) as a tan solid. 1H-NMR (CDCl3) δ 6.54 (s, 1H), 6.47 (s, 1H), 5.80 (br s, 1H), 3.82 (s, 3H), 3.73 (s, 2H), 3.71 (br s, 2H), 3.53 (q, J=6.3 Hz, 2H), 2.96 (t, J=6.1 Hz, 2H); LC/MS (ESI+): 207.13 (M+H).

Provenance & Evidence