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

HRID 365409Notes

Reaction equation

HRID 365409 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 in portions with 7 ml of hydrazine hydrate and 2.5 g of Raney nickel 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).

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-917b596cf3a14de4835f93e870daf4c6
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

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