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

HRID 3503Notes

Reaction equation

HRID 3503 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-9414b7fc6c2b4a35b0deb6bc71152998
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

Loading…