Hydrazine hydrate (1:1) → HCID 11245990, compound

HRID 2421835Notes

Reaction equation

HRID 2421835 reaction equation
[CH:1]1([NH:4][C:5]([N:7]2[C:13]([CH3:14])=[CH:12][C:11]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:10]=3[C:9]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([CH3:29])[CH:21]=3)=[N:8]2)=[O:6])[CH2:3][CH2:2]1.O.NN>CO.ClCCl.[Ni]>[CH:1]1([NH:4][C:5]([N:7]2[C:13]([CH3:14])=[CH:12][C:11]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:10]=3[C:9]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:29])[CH:21]=3)=[N:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67243228HCID 67243228, compound

Product 1

HCID 11245990HCID 11245990, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.38 g (3.35 mmoles) of 8-chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-3H-2,3-benzodiazepine-3-carboxylic acid cyclopropyl amide is dissolved in the mixture of 28 ml of methanol and 14 ml of dichloromethane, and about 1.0 g of wet Raney nickel catalyst and 0.42 ml (8.37 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 dichloromethane, the filtrate is evaporated and the residue is solidified by rubbing with 10 ml of water. The crude product is recrystallized from ethanol. Thus 1.15 g (90%) of the desired compound melting at 233-236° C. is obtained.

Workup

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

Sources & evidence

ORD record
ord-bf06418013404415a496beb2b0745655
Source dataset
uspto-grants-2011_06
Patent number
US07960375B2

Reaction notes

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