2-Nitro-4-(trifluoromethyl)benzamide → 2-Amino-4-(trifluoromethyl)benzamide

HRID 1424407Notes

Reaction equation

HRID 1424407 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O>CO.[OH-].[Pd+2].[OH-]>[NH2:1][C:4]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 27757792-Nitro-4-(trifluoromethyl)benzamide

Product 1

HCID 697392-Amino-4-(trifluoromethyl)benzamideYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 2-nitro-4-(trifluoromethyl)benzamide (1000 mg, 4.27 mmol), in MeOH (15 mL) was added palladium hydroxide 20% by weight (230 mg) and the mixture was stirred at rt overnight. The reaction mixture was filtered through Celite washing with MeOH. The crude mixture was concentrated in vacuo to afford 2-amino-4-(trifluoromethyl)benzamide (840 mg, 96%). LC-MS (ESI) m/z 205 (M+Na)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashing with MeOH
  3. concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-45c4b88a4a4e4626a81b247268db6546
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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