Hydrazine hydrate (1:1) → 8-amino-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

Participants

Reaction Steps

Added 65 mL of ethanol, 10% Palladium on activated carbon (50% wet with water for safety) (513 mg), and hydrazine monohydrate (965 ul) to 8-Nitro-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (1.024 g, 4.966 mmol). Heated reaction to 60° C. for 16 hours. Filtered reaction through Celite, and concentrated under reduced pressure. Purified with normal phase silica gel chromatography to obtain a white solid, 8-Amino-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (799 mg, 91%). LCMS: m/z=177.03 (M+H+), 1H NMR (400 MHz, CD3OD) δ 7.00 (d, 1H, J=8.1 Hz), 6.96 (m, 1H), 6.80 (m, 1H), 3.33 (m, 3H), 3.06 (m, 2H), 2.71 (m, 2H), 1.96 (m, 2H).

Provenance & Evidence