Hydrazine → 3-Chloro-10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 439951Notes

Reaction equation

HRID 439951 reaction equation
[Cl:1][C:2]1[N:11]2[C:5]([CH2:6][N:7]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][C:20]([NH:23][N+]([O-])=O)=[CH:19][CH:18]=3)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10]2)=[CH:4][CH:3]=1.NN>[Pd].C(O)C>[Cl:1][C:2]1[N:11]2[C:5]([CH2:6][N:7]([C:16](=[O:27])[C:17]3[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=3)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 218369643-chloro-10,11-di-hydro-10-(4-nitroaminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 218370993-Chloro-10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1 mmol of 3-chloro-10,11-dihydro-10-(4-nitroaminobenzoyl)-5H-pyrrolo[2,1-c][1,4]-benzodiazepine, 2.5 mmol of anhydrous hydrazine, 50 mg of palladium on carbon and 10 ml of ethyl alcohol is refluxed for 1.5 hours. The mixture is filtered through diatomaceous earth and the filtrate concentrated to dryness to give the desired product as a solid.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. filtrationThe mixture is filtered through diatomaceous earth
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-a68d7f40141e4611ac58aa95090677d6
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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