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

HRID 1684515Notes

Reaction equation

HRID 1684515 reaction equation
C1(N[N:8]=[C:9]2[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:10]2=[O:32])C=CC=CC=1>C(O)(=O)C.[Zn]>[NH2:8][CH:9]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[N:11]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]1=[O:32]

Participants

4

Reactant 1

HCID 544011821-(3-Methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,3,4-(5H)-trione-3-(phenylhydrazone)

Product 1

HCID 190394433-Amino-1-(3-methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dioneYield 74.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. filtrationAfter 1 h the mixture was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was redissolved with DCM (200 ml) and water (100 ml)
  4. additionthe mixture was cautiously neutralised by portionwise addition of solid sodium carbonate
  5. extractionThe mixture was extracted with DCM
  6. washthe combined organic extracts were washed with saturated brine
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed with DCM-MeOH (1→8%) as eluent

Sources & evidence

ORD record
ord-15a32cbff78040f2b04ad3e44e041904
Source dataset
uspto-grants-1997_06
Patent number
US05641775

Reaction notes

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