Flutamide → N-[4-Amino-3-(trifluoromethyl)phenyl]-2-methylpropanamide

HRID 614293

Reaction equation

HRID 614293 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[C:16]([F:19])([F:18])[F:17])([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[C:16]([F:17])([F:18])[F:19]

Participants

4

Reactant 1

HCID 3397Flutamide

Product 1

HCID 16776651N-[4-Amino-3-(trifluoromethyl)phenyl]-2-methylpropanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenate, at approximately 3 atmospheres, a mixture of 8.3 g. of 4'-nitro-3'-trifluoromethylisobutyranilide in 100 ml. of ethanol containing 0.5 g. of 5% palladium on charcoal. Filter and remove the solvent, obtaining 4'-amino-3'-trifluoromethylisobutyranilide, m.p. 114.5°-116° C.

Workup

  1. additionHydrogenate, at approximately 3 atmospheres, a mixture of 8.3 g
  2. filtrationFilter
  3. customremove the solvent

Sources & evidence

ORD record
ord-02a1de3a5d9142449202be4dd9fa9066
Source dataset
uspto-grants-1979_03
Patent number
US04144270

Linked notes

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