Sodium Hydroxide → 7-Methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Steps

2,2,2-Trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone (7.0 g, 0.022 mol) was dissolved in acetonitrile (150 mL). A 50% aqueous solution (70 mL) of sodium hydroxide was added at 0° C. After 10 minutes the reaction mixture allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was partitioned between saturated Na2CO3 and dichloromethane, extracted, dried (MgSO4), filtered, and concentrated, to provide 7-methoxy-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.43 g, 89%). 1H-NMR (CDCl3) δ 7.67 (s, 1H), 6.82 (s, 1H), 3.93 (s, 3H), 2.75-3.05 (m, 8H), 1.90 (br s, 1H); LC/MS (ESI+): 223.03 (M+H).

Provenance & Evidence