Hydrazine hydrate (1:1) → HCID 11394118, compound

HRID 2421834Notes

Reaction equation

HRID 2421834 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:11]([CH3:12])=[CH:10][C:9]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([CH3:27])[CH:19]=2)=[N:6]1)=[O:4].O.NN>CO.ClCCl.[Ni]>[CH3:1][NH:2][C:3]([N:5]1[C:11]([CH3:12])=[CH:10][C:9]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH3:27])[CH:19]=2)=[N:6]1)=[O:4]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67241489HCID 67241489, compound

Product 1

HCID 11394118HCID 11394118, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

10.89 g (28 mmoles) 8-chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-3H-2,3-benzodiazepine 3-carboxylic acid methyl amide are dissolved in the mixture of 190 ml of methanol and 95 ml of dichloromethane, and about 5.0 g of wet Raney nickel catalyst and 3.5 ml (70 mmoles) of 98% hydrazine hydrate are subsequently added to it under vigorous stirring. The mixture is stirred for further 1 hour, the catalyst is filtered off, washed with dichloro-methane, the filtrate is evaporated and the residue is solidified by rubbing with 100 ml of water. The crude product is recrystallized from ethanol. Thus 7.73 g (78%) of the desired compound melting at 210-212° C. are obtained.

Workup

  1. additionare subsequently added to it under vigorous stirring
  2. filtrationthe catalyst is filtered off
  3. washwashed with dichloro-methane
  4. customthe filtrate is evaporated
  5. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-f389e4b753be4c20bac71c0b2398838a
Source dataset
uspto-grants-2011_06
Patent number
US07960375B2

Reaction notes

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