Hydrochloric Acid → HCID 9839097, compound

Participants

Reaction Steps

To a suspension of 7,8-methylenedioxy-1-(4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (167 mg, 0.51 mmol) in ethanol (8 mL) was added Raney Ni (430 mg), hydrazine hydrate (200 μL, 3.5 mmol) and 2N HCl (150 μL, 0.3 mmol). The mixture was stirred at room temperature for 17 h. The solid Ni was filtered out. The filtrate was concentrated in vacuo and the resulting residue was separated by chromatography (1:4 hexane/EtOAc) to afford the title compound as a yellow solid (110 mg, 0.37 mmol, 73%), mp: 242°-244° C. 1H NMR (CDCl3) 8.32 (s, 1H), 7.41 (d, 2H, J=8.5), 6.81 (s, 1H), 6.70 (s, 1H), 6.68 (d, 2H, J=8.5), 6.02 (s, 2H), 3.94 (brs, 2H), 3.42 (s, 2H). Anal. Calcd. for C16H13N3O3.0.25H2O: C, 64.10; H, 4.54; N, 14.02. Found C, 64.32; H, 4.37; N, 13.48.

Provenance & Evidence