2,2,2-trifluoro-N-[3-(4-nitrophenoxy)phenyl]acetamide → N-[3-(4-aminophenoxy)phenyl]-2,2,2-trifluoroacetamide

HRID 2190456Notes

Reaction equation

HRID 2190456 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:7]=1)=[O:4]>C(OCC)(=O)C.[C].[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:22])[F:23])[CH:11]=[CH:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 866553932,2,2-trifluoro-N-[3-(4-nitrophenoxy)phenyl]acetamide

Product 1

HCID 86655394N-[3-(4-aminophenoxy)phenyl]-2,2,2-trifluoroacetamideYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-[3-(4-nitrophenoxy)phenyl]acetamide (13.0 g, 39.8 mmol) in ethyl acetate (400 mL) was added 10% palladium-carbon (10 g), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (11.7 g, 99%) as a pale-gray amorphous substance. The obtained compound was used in the next reaction without a further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c41d34d0dd64ca5886b486b03aa8184
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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