3-(Trifluoromethyl)aniline → 5-Oxo-3-(3-(trifluoromethyl)phenylamino)cyclohex-3-enecarboxylic acid

HRID 517191Notes

Reaction equation

HRID 517191 reaction equation
O=[C:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]([C:9]([OH:11])=[O:10])[CH2:3]1.[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[OH-].[Na+]>O.CN(C)C=O>[O:8]=[C:6]1[CH2:5][CH:4]([C:9]([OH:11])=[O:10])[CH2:3][C:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=2)=[CH:7]1

Participants

7

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 14798Sodium HydroxideHCID 2733225Ytterbium triflateHCID 143714583,5-Dioxocyclohexane-1-carboxylic acid

Product 1

HCID 867323105-Oxo-3-(3-(trifluoromethyl)phenylamino)cyclohex-3-enecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dioxocyclohexanecarboxylic acid (1.00 g, 6.41 mmol), 3-(trifluoromethyl)aniline (880 μL, 1.14 g, 4.05 mmol), Ytterbium(III) trifluormethanesulfonate (20 mg, 32 μmol, 0.5 mol %) and N,N-dimethylformamide (3 mL) is stirred at room temperature over night. Water and aqueous sodium hydroxide are added and the mixture is washed with diethyl ether. The organic layer is discarded, and the aqueous layer is acidified with aqueous hydrogen chloride and extracted with diethyl ether. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. Yield: 1.30 g; ESI mass spectrum [M+H]+=300, Retention time HPLC: 1.08 min (V001—006).

Workup

  1. washthe mixture is washed with diethyl ether
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custom1.08 min (V001—006)

Sources & evidence

ORD record
ord-e11995f4bf174f3eb075eea376459803
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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