HCID 59807107, compound → HCID 59807136, compound

Participants

Reaction Steps

1-(2-(dimethylamino)ethyl)-9-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (100 mg, 0.361 mmol) was stirred to dissolve in a mixture of ethanol (4 mL) and THF (3 mL). To this solution was added palladium on carbon, 10 wt %, (40 mg) as a solid. The black suspension was stirred under hydrogen gas for 3 h. When TLC analysis showed that the starting material was consumed the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated and then chromatographed on silica gel in 10% 2 N NH3/MeOH in dichloromethane. Yield 90 mg (quantitative). 1H NMR (DMSO-d6) δ 6.86 (d, 1H, J=8.1 Hz), 6.53 (d, 1H, J=3.0 Hz), 6.38 (dd, 1H, J=8.1, 3.0 Hz), 5.02 (brs, 2H), 2.50 (m, 2H), 2.25 (m, 2H), 1.8-2.2 (m, 10H); ESI-MS (m/z, %): 248 (MH+, 58), 203 (100).

Provenance & Evidence