Hydrazine hydrate (1:1) → HCID 11405060, compound

HRID 2421833Notes

Reaction equation

HRID 2421833 reaction equation
[C:1]([N:4]1[C:10]([CH3:11])=[CH:9][C:8]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([CH3:26])[CH:18]=2)=[N:5]1)(=[O:3])[CH3:2].O.NN>CO.ClCCl.[Ni]>[C:1]([N:4]1[C:10]([CH3:11])=[CH:9][C:8]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([CH3:26])[CH:18]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11428649HCID 11428649, compound

Product 1

HCID 11405060HCID 11405060, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.78 g (2.1 mmoles) of 3-acetyl-8-chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-3H-2,3-benzodiazepine are dissolved in the mixture of 15 ml of methanol and 15 ml of dichloromethane, and about 0.5 g of wet Raney-nickel catalyst and 0.26 ml (5.25 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 15 ml of water. The crude product is recrystallized from ethanol. Thus 0.56 g (79%) of the desired compound melting at 209-211° 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-705999548eaa4a278e0894c535941e4d
Source dataset
uspto-grants-2011_06
Patent number
US07960375B2

Reaction notes

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