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

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Reaction Steps

To a solution of N-[2-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide (100 mg, 0.3 mmol) in methanol (20 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 N-[2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethyl]-acetamide (90 mg, 100%) as a yellow oil, which was used without further purification. 1H-NMR (CDCl3) δ 6.59 (br s, 1H), 6.53 (s, 1H), 6.48 (s, 1H), 3.82 (s, 3H), 3.50-4.40 (br s, 2H), 3.40 (m, 2H), 2.65-2.93 (m, 10H), 2.02 (s, 3H); LC/MS (ESI+): 278.25 (M+H).

Provenance & Evidence