Hydrazine hydrate (1:1) → HCID 10271673, compound

HRID 457474Notes

Reaction equation

HRID 457474 reaction equation
[Cl:1][C:2]1[C:3]([Cl:28])=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([CH3:21])[CH:13]=3)=[N:10][N:9]([C:22](=[O:25])[CH2:23][CH3:24])[CH:8]([CH3:26])[CH2:7][C:6]=2[CH:27]=1.O.NN>CO.ClCCl.[Ni]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:5]3[CH:4]=[C:3]([Cl:28])[C:2]([Cl:1])=[CH:27][C:6]=3[CH2:7][CH:8]([CH3:26])[N:9]([C:22](=[O:25])[CH2:23][CH3:24])[N:10]=2)=[CH:13][C:14]=1[CH3:21]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933122HCID 17933122, compound

Product 1

HCID 10271673HCID 10271673, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4.2 g (10 mmoles) of (±)-4,5-dihydro-7,8-dichloro-4-methyl-1-(3-methyl-4-nitrophenyl)-3-propionyl-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 purified by chromatography over a column containing silica gel and using a mixture of ethyl acetate and hexane, then the product is recrystallized from acetonitrile. Thus, 1.99 g (56%) of the title compound are obtained in the form of pale yellow solids melting at 106–108° 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 acetonitrile

Sources & evidence

ORD record
ord-1136d98e24ed4acc90bab42866f7d181
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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