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

Participants

Reaction Steps

A solution of 4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (1.42 g, 8.81 mmol) in conc. H2SO4 (25 mL) was treated with fuming HNO3 (414 μL, 8.81 mmol) at −5 to −10° C. (ice/MeOH). The resulting solution was stirred at the same temperature for 30 minutes. The reaction was quenched with the addition of crushed ice. The resulting suspension was diluted with H2O (50 mL) and filtered. The solid was washed with 4×50 mL H2O, collected and dried under reduced pressure overnight. Yield: 1.0 g, 55.1%. 1H-NMR (DMSO-d6) δ 10.08 (s, 1H), 8.19 (d, J=2.4 Hz, 1H), 8.11 (dd, J=2.4, 8.7 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H), 2.83-2.79 (m, 2H), 2.26-2.13 (m, 4H). MS (EI): 206 (M+).

Provenance & Evidence