7-Nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide → 7-Amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide

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Reaction Steps

7-Nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide (82 mg, 0.312 mmol) was placed in methanol (5 mL) and 10% palladium on carbon (8.2 mg) was added. The reaction was hydrogenated at 40 psi for 1 hour. The mixture was then filtered through celite and concentrated under reduced pressure to obtain 7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-carboxylic acid dimethylamide as a clear thin film (72 mg, 100%). LCMS (m/e) 234 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.91 (d, 1H, J=7.6 Hz), 6.58-6.49 (m, 2H), 3.75 (bs, 2H), 3.42-3.34 (m, 4H), 2.93-2.82 (m, 4H), 2.85 (s, 3H), 2.84 (s, 3H).

Provenance & Evidence