N-tert-Butyl-4-nitrobenzamide → 4-amino-N-(tert-butyl)benzamide

HRID 1934344Notes

Reaction equation

HRID 1934344 reaction equation
[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 591441N-tert-Butyl-4-nitrobenzamide

Product 1

HCID 41264084-amino-N-(tert-butyl)benzamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ten percent Pd/C (0.1003 g) was added to a solution of N-t-butyl-4-nitrobenzamide (0.7349 g, 3.31 mmol) in ethyl acetate (10 ml), and stirred under a hydrogen atmosphere for 1 hour. The reaction mixture was filtered through Celite® bed and the solvent was evaporated. The residue was purified by silica gel chromatography (hexane/ethyl acetate/triethylamine=50/100/1) to give the title compound (0.6156 g; 97%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite® bed
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate/triethylamine=50/100/1)

Sources & evidence

ORD record
ord-c829a97455744069971924ed0881cec4
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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