1-(3-Methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,3,4-(5H)-trione-3-(phenylhydrazone) → 3-Amino-1-(3-methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione

Participants

Reaction Steps

Zinc dust (26 g) was added to a suspension of 1-(3-methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,3,4-(5H)-trione 3-(phenylhydrazone) (20.2 g) in 97% acetic acid (260 ml) at 23° under nitrogen. After 1 h the mixture was filtered and the filtrate evaporated. The residue was redissolved with DCM (200 ml) and water (100 ml) and the mixture was cautiously neutralised by portionwise addition of solid sodium carbonate. The mixture was extracted with DCM and the combined organic extracts were washed with saturated brine, dried and evaporated. The residue was chromatographed with DCM-MeOH (1→8%) as eluent to give the title compound (11.9 g) as a yellow oil.

Provenance & Evidence