Hydrazine hydrate (1:1) → HCID 10269626, compound

HRID 457471Notes

Reaction equation

HRID 457471 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[CH2:6][CH:7]([CH3:25])[N:8]([C:21](=[O:24])[CH2:22][CH3:23])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([CH3:20])[CH:12]=3)[C:4]=2[CH:3]=1.O.NN>CO.ClCCl.[Ni]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:4]3[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=3[CH2:6][CH:7]([CH3:25])[N:8]([C:21](=[O:24])[CH2:22][CH3:23])[N:9]=2)=[CH:12][C:13]=1[CH3:20]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17933121HCID 17933121, compound

Product 1

HCID 10269626HCID 10269626, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3.86 g (10 mmoles) of (±)-4,5-dihydro-8-chloro-4-methyl-1-(3-methyl-4-nitrophenyl)-3-propionyl-3H-2,3-benzodiazepine are dissolved in a mixture of 80 cm3 of methanol and 13 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 cream coloured solids melting at 152–154° 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-e81b63e256d249c5ae963d0ccb3352f8
Source dataset
uspto-grants-2007_03
Patent number
US07189711B2

Reaction notes

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