Hydrazine → 6,7-Dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 1739893Notes

Reaction equation

HRID 1739893 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]3[CH:21]=[CH:22][CH:23]=[C:13]3[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]3[CH:21]=[CH:22][CH:23]=[C:13]3[CH2:12][CH2:11]2)=[O:9])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 218371116,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Product 1

HCID 218371566,7-Dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5 mmol of 6,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 3 hours
  3. filtrationThe reaction mixture is filtered through diatomaceous earth
  4. concentrationThe filtrate is concentrated in vacuo to a residue which
  5. dissolutionis dissolved in methylene chloride
  6. concentrationThe filtrate is concentrated vacuo

Sources & evidence

ORD record
ord-b16b6791331e440baae49e56097578c7
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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