4-(4-Nitrophenyl)cyclohexanone → 4-(4-Aminophenyl)cyclohexan-1-one

HRID 2408513Notes

Reaction equation

HRID 2408513 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 212604964-(4-Nitrophenyl)cyclohexanone

Product 1

HCID 233718944-(4-Aminophenyl)cyclohexan-1-oneYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(4-nitro-phenyl)-cyclohexanone (0.512 g, 2.34 mmol, as prepared in the previous step) in EtOH (50 mL) was hydrogenated under the following conditions on an H-cube apparatus fitted with a 30 mm CatCart™ 5% Pd/C cartridge: 40° C., 40 bar H2, flow rate 1 mL/min. The solvent was evaporated in vacuo. Silica gel chromatography of the residue with 25% EtOAc-hexane on a 20-g Isolute SPE column (FlashMaster system) afforded the title compound (0.140 g, 32%) as a colorless glassy solid. Mass spectrum (ESI, m/z): Calcd. for C12H15NO, 190.1 (M+H), found 190.2.

Workup

  1. custom40° C., 40 bar H2, flow rate 1 mL/min
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f07fade773514a4c9fd109cf147fce0e
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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