Hydrazine hydrate (1:1) → HCID 9968932, compound

HRID 457472Notes

Reaction equation

HRID 457472 reaction equation
[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][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]([Cl:26])[CH:18]=2)=[N:5]1)(=[O:3])[CH3:2].O.NN>CO.ClCCl.[Ni]>[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][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]([Cl:26])[CH:18]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933119HCID 17933119, compound

Product 1

HCID 9968932HCID 9968932, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3.93 g (10 mmoles) of (±)-3-acetyl-4,5-dihydro-8-chloro-1-(3-chloro-4-nitrophenyl)-4-methyl-3H-2,3-benzodiazepine are dissolved in a mixture of 30 cm3 of methanol and 30 cm3 of dichloromethane, then 3.0 g of wet Raney nickel catalyst and, under vigorous stirring, 1.7 cm3 (35 mmoles) of 98% hydrazine hydrate are added. The reaction mixture is stirred for further 45 minutes, the catalyst is filtered, washed with dichloromethane, the filtrate is evaporated, and the residue is rubbed with 50 cm3 of water to obtain solid matter. The crude product is purified by chromatography over a column containing silica gel and using a mixture of ethyl acetate and hexane, then the product is recrystallized from a mixture of ethyl acetate and hexane. Thus, 1.03 g (30%) of the title compound are obtained in the form of yellow solids melting at 143–144° C.

Workup

  1. filtrationthe catalyst is filtered
  2. washwashed with dichloromethane
  3. customthe filtrate is evaporated
  4. customto obtain solid matter
  5. customThe crude product is purified by chromatography over a column
  6. additioncontaining silica gel
  7. additiona mixture of ethyl acetate and hexane
  8. customthe product is recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-fc2d6ad884e84a5c98391cbf74ba3bf5
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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