Hydrazine hydrate (1:1) → 8-Amino-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Participants

Reaction Conditions

Reaction Steps

To a solution of Diethyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (25.0 g, 0.095 mol) and 10% palladium on carbon (2.0 g) in ethanol (600 mL) was slowly added hydrazine hydrate (150 mL) and heated to 75° C. for 5 hr. After evaporation, toluene (50 mL) and ethanol (50 mL) were added and distilled leaving 8-Amino-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a yellow solid (22.75 g, 85%). Mp 140-141° C.; LCMS (m/e) 233 (M); 1H-NMR (DMSO, 400 MHz) δ 7.14-7.12 (d, 1H, J=8.85 Hz), 6.10-6.09 (d, 1H, J=6.82 Hz), 5.35 (s, 2H), 3.46-3.41 (q, 2H, 7.07 Hz), 3.19-3.16 (t, 2H, J=5.31 Hz), 3.09-3.03 (q, 2H, J=7.07 Hz), 1.12-1.06 (q, 6H, J=7.07 Hz).

Provenance & Evidence