Hydrazine hydrate (1:1) → HCID 10177514, compound

HRID 457473Notes

Reaction equation

HRID 457473 reaction equation
[C:1]([N:4]1[CH:10]([CH3:11])[CH2:9][C:8]2[CH:12]=[C:13]([Cl:17])[C:14]([Cl:16])=[CH:15][C:7]=2[C:6]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([CH3:27])[CH:19]=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]([Cl:17])[C:14]([Cl:16])=[CH:15][C:7]=2[C:6]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH3:27])[CH:19]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933116HCID 17933116, compound

Product 1

HCID 10177514HCID 10177514, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4.06 g (10 mmoles) of (±)-3-acetyl-4,5-dihydro-7,8-dichloro-1-(3-methyl-4-nitrophenyl)-4-methyl-3H-2,3-benzodiazepine are dissolved in a mixture of 55 cm3 of methanol and 55 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 recrystallized from a mixture of ethyl acetate and hexane. Thus, 3.27 g (87%) of the title compound are obtained in the form of yellow ochre solids melting at 127–129° 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 recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-05f146286ebd4f7fa5e90f8071bc0f74
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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