Hydrazine hydrate (1:1) → (-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene

HRID 1954067Notes

Reaction equation

HRID 1954067 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].O.NN>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15389590(+/-)-cis1,2-Dimethoxy-4-(2-nitrocyclohexyl)benzene

Product 1

HCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

8.5 g of (+/-)-cis-1,2-dimethoxy-4-(2-nitrocyclohexyl)benzene are dissolved in 400 ml of methanol and treated with 7 ml of hydrazine hydrate and 2.5 g of Raney nickel in portions at RT in the course of 8 h. After stirring overnight at RT, the reaction mixture is filtered, the filtrate is concentrated and the residue is chromatographed on silica gel using a mixture of toluene/ethyl acetate/triethylamine=4/2/0.5. The title compound is obtained as an oil.

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is chromatographed on silica gel using
  4. additiona mixture of toluene/ethyl acetate/triethylamine=4/2/0.5

Sources & evidence

ORD record
ord-cc92d9e348714dbe8fb2a5b16ae4f89e
Source dataset
uspto-grants-2000_09
Patent number
US06121279

Reaction notes

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