2-methyl-N-[2-nitro-4-(trifluoromethyl)phenyl]propanamide → N-[2-Amino-4-(trifluoromethyl)phenyl]-2-methylpropanamide

HRID 1288320Notes

Reaction equation

HRID 1288320 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:5]=1[NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:5]=1[NH:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 39579122-methyl-N-[2-nitro-4-(trifluoromethyl)phenyl]propanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 16774420N-[2-Amino-4-(trifluoromethyl)phenyl]-2-methylpropanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Shake 85 g. of 2'-nitro-4'-trifluoromethylisobutyranilide in 1.0 liter of ethanol containing 3.0 g. of 5% palladium on charcoal in a parr shaker under approximately 50 lbs. per square inch hydrogen pressure for twenty-four hours. Filter, remove the ethanol and recrystallize from a dichloromethane-chloroform-hexane mixture, obtaining the product of this step.

Workup

  1. filtrationFilter
  2. customremove the ethanol
  3. customrecrystallize from a dichloromethane-chloroform-hexane mixture
  4. customobtaining the product of this step

Sources & evidence

ORD record
ord-0f249124da3a4f41b82e5e36446a9729
Source dataset
uspto-grants-1976_10
Patent number
US03987182

Reaction notes

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