2-(7-Methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide → 2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethylacetamide

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Reaction Steps

To a solution of 2-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide (767 mg, 1.75 mmol) in methanol (30 mL) was added palladium 10% wt on Carbon (50% wet; 100 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 the crude product, which was purified by flash chromatography on SiO2 (MeOH/dichloromethane 0-6%) to give 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide (332 mg, 69%) as a white solid. 1H-NMR (CDCl3) δ 6.54 (s, 1H), 6.48 (s, 1H), 3.81 (s, 3H), 3.53 (br s, 2H), 3.23 (s, 2H), 3.13 (s, 3H), 2.96 (s, 3H), 2.80 (m, 4H), 2.65 (m, 4H); LC/MS (ESI+): 278.67 (M+H).

Provenance & Evidence