Hydrazine hydrate (1:1) → HCID 18439652, compound

HRID 457475Notes

Reaction equation

HRID 457475 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]([Cl: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]([Cl:27])[CH:19]=2)=[N:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933120HCID 17933120, compound

Product 1

HCID 18439652HCID 18439652, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4.26 g (10 mmoles) of (±)-3-acetyl-4,5-dihydro-7,8-dichloro-1-(3-chloro-4-nitrophenyl)-4-methyl-3H-2,3-benzodiazepine are dissolved in a mixture of 40 cm3 of methanol and 40 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 acetonitrile. Thus, 2.80 g (71%) of the title compound are obtained in the form of butter coloured 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 acetonitrile

Sources & evidence

ORD record
ord-22f69210418c44909bceff05b854f951
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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