N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide → N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 1038661Notes

Reaction equation

HRID 1038661 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[N+:21]([O-])=O>[Pd].C(O)C>[NH2:21][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N-(4-methyl-3-nitro-phenyl)-3-trifluoromethyl-benzamide (9.91 g, 30.6 mmol) and 10% palladium on charcoal (990 mg) in ethanol (180 ml) is hydrogenated at atmospheric pressure and room temperature. After 2 h the reaction is complete, the catalyst is removed by filtration through Celite, and the filtrate is evaporated to dryness. Recrystallization of the crude product from ethyl acetate/hexanes followed by vacuum drying at 45° C. overnight affords the title compound as fluffy light grey needles: HPLC: tR=5.38 min (purity: >99%, gradient A), ESI-MS: 295.3 [MH]+

Workup

  1. customis hydrogenated at atmospheric pressure and room temperature
  2. customthe catalyst is removed by filtration through Celite
  3. customthe filtrate is evaporated to dryness
  4. customRecrystallization of the crude product from ethyl acetate/hexanes
  5. customdrying at 45° C. overnight

Sources & evidence

ORD record
ord-ad0394b2d54c4b50925131c22bea3b2f
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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