N-Cyclohexyl-N-methyl-2-nitrobenzamide → 2-amino-N-cyclohexyl-N-methylbenzamide

HRID 852234Notes

Reaction equation

HRID 852234 reaction equation
[CH:1]1([N:7]([CH3:19])[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Ni]>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]([N:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:19])=[O:18]

Participants

4

Reactant 1

HCID 799283N-Cyclohexyl-N-methyl-2-nitrobenzamide

Product 1

HCID 8453022-amino-N-cyclohexyl-N-methylbenzamideYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of the crude N-cyclohexyl-N-methyl-2-nitrobenzamide (1.05 g, 4 mmol) and a catalytic amount of Raney-Ni® in methanol (25 ml) was stirred overnight under hydrogen at room temperature. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was dried (MgSO4) and the solvents removed under reduced pressure to give (0.89 g, 96%) of the title compound as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe resulting crude was dissolved in dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-681d2c642a5d45a682ebb157387e4e2e
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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