1-(2-Nitrophenyl)cyclohexan-1-ol → 1-(2-Aminophenyl)cyclohexan-1-ol

HRID 2223126Notes

Reaction equation

HRID 2223126 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([O-])=O.[H][H]>[Ni].CCO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 210728061-(2-Nitrophenyl)cyclohexan-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 135545281-(2-Aminophenyl)cyclohexan-1-ol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5.20 g (16.45 mmol) of 1-(2-nitrophenyl)cyclohexanol and 500 mg of Raney nickel in EtOH (70 mL) is hydrogenated at RT and under 3 bar hydrogen pressure for 4 hours. The catalyst is filtered off through CELITE® filter aid and the filtrate is evaporated down in vacuo. The residue is recrystallized from hexane. Yield: 1.53 g (49%); Rf=0.38 (silica gel, hexane/EtOAc 4:1); ESI-MS: [M+H−H2O]+=174.

Workup

  1. filtrationThe catalyst is filtered off through CELITE®
  2. filtrationfilter aid
  3. customthe filtrate is evaporated down in vacuo
  4. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-31ff24a284844bde816e72d082ad65b7
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

Loading…