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

HRID 3554Notes

Reaction equation

HRID 3554 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 in 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 in vacuo

Sources & evidence

ORD record
ord-8f3157e129004e4ebb3ee2889687de22
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

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