Hydrazine hydrate (1:1) → HCID 18439653, compound

HRID 457479Notes

Reaction equation

HRID 457479 reaction equation
[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][C:8]2[CH:12]=[C:13]([Br:18])[C:14]([O:16][CH3:17])=[CH:15][C:7]=2[C:6]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([Cl:28])[CH:20]=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]=[C:13]([Br:18])[C:14]([O:16][CH3:17])=[CH:15][C:7]=2[C:6]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([Cl:28])[CH:20]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933124HCID 17933124, compound

Product 1

HCID 18439653HCID 18439653, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4.66 g (10 mmoles) of (±)-3-acetyl-7-bromo-4,5-dihydro-1-(3-chloro-4-nitrophenyl)-4-methyl-8-methoxy-3H-2,3-benzodiazepine are dissolved in a mixture of 45 cm3 of methanol and 45 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 boiling in 50 ml of acetonitrile. Thus, 3.52 g (81%) of the title compound are obtained in the form of white solids melting at 235–237° 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

Sources & evidence

ORD record
ord-1d23b675dfc84a7d872558d53b1ab169
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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