Nitric Acid → 8-Nitro-1,2,4,5-tetrahydro-benzo[c]azepin-3-one

Participants

Reaction Conditions

Reaction Steps

At 0° C., 1,2,4,5-tetrahydro-benzo[c]azepin-3-one (1 g, 6.2 mmol) was added to fuming nitric acid (3 mL) and the mixture was slowly warmed up to 25° C. during 1 h. The mixture was stirred at ambient temperature for 1 h and poured onto ice. The mixture was extracted with dichloromethane (3×50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The crude mixture was then recrystallized from dichloromethane/hexane to give 8-nitro-1,2,4,5-tetrahydro-benzo[c]azepin-3-one (0.2 g). 1H NMR (300 MHz, CDCl3) δ 8.12 (dd, 1H), 8.03 (d, 1H), 7.37 (d, 1H), 4.47 (d, 2H), 3.2 (m, 2H), 2.8 (m, 2H).

Provenance & Evidence