Nitric Acid → 7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

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Reaction Conditions

Reaction Steps

1,3,4,5-Tetrahydro-benzo[b]azepin-2-one (406 mg, 2.52 mmol) was added to a cooled (0° C.) mixture of nitric acid (5 ml) and sulfuric acid (7 ml). The mixture was stirred at 0° C. for 15 minutes, then poured into water (50 ml) and extracted with ethyl acetate (50 ml). The organic phase was washed once with aqueous sodium bicarbonate and once with water, and concentrated to a yellow solid. Trituration with ether afforded 7-Nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as an off-white solid, 276 mg. (53% yield) 1H NMR (400 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.19 (s, 1H), 8.09-8.16 (m, 1H), 7.12-7.28 (m, 1H), 2.78-2.86 (m, 2H), 2.20-2.38 (m, 4H); MS (m/e) 207 (M+1).

Provenance & Evidence