Sodium Hydroxide → 4-Trifluoroacetylaniline

HRID 28628Notes

Reaction equation

HRID 28628 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)=[O:4].[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[C:2]([F:1])([F:14])[F:15])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 110639262,2,2-Trifluoro-1-(4-nitrophenyl)ethanone

Product 1

HCID 901384-TrifluoroacetylanilineYield 19.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 2,2,2-trifluoro-1-(4-nitro-phenyl)-ethanone (4.5 g, 20.5 mmol) in concentrated hydrochloric acid (15 ml) and water (15 ml) was added tin (II) chloride (14 g, 74 mmol). After stirring for 24 hours, the mixture was adjusted to pH 10 by addition of aqueous sodium hydroxide solution (50%) and extracted with ethyl acetate. The organic extract was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:5) followed by recrystallization (ethyl acetate-hexane) to afford 1-(4-amino-phenyl)-2,2,2-trifluoro-ethanone (750 mg, 19% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:5)
  5. customfollowed by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4c0bbe7599784a49a6c3c401377c1fa1
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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