4-Fluoro-1-nitro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocycloheptene → 4-Fluoro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten-1-ylamine

Participants

Reaction Steps

To a solution of 4-fluoro-1-nitro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocycloheptene (158 mg, 0.746 mmol) in EtOAc (10 mL) was added a slurry of 10% Pd/C (30 mg) in IMS (1 mL) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 18 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording the title compound as a brown solid (131.5 mg, 97%). 1H NMR (CDCl3, 300 MHz): 6.46 (1H, dd, J=10.2, 8.6 Hz), 6.35 (1H, dd, J=8.7, 5.1 Hz), 4.25 (2H, t, J=5.8 Hz), 3.36-3.32 (5H, bs & m), 2.06 (2H, quintet, J=5.8 Hz)

Provenance & Evidence