Water → 4-(trifluoromethyl)nicotinonitrile

HRID 1744269Notes

Reaction equation

HRID 1744269 reaction equation
C[O-].[Na+].[F:4][C:5]([F:16])([F:15])[C:6](=O)[CH:7]=[CH:8][NH:9][CH:10]=[CH:11][C:12]#[N:13].O.CCCCCC.C(OCC)(=O)C>CO>[C:12]([C:11]1[CH:10]=[N:9][CH:8]=[CH:7][C:6]=1[C:5]([F:16])([F:15])[F:4])#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 21226206Ethyl acetate hexaneHCID 731022503-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

Product 1

HCID 27367434-(trifluoromethyl)nicotinonitrileYield 56.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 28% sodium methoxide (580 mg, 3.0 mmol), a solution prepared by dissolving 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 380 mg, 2.0 mmol) in methanol (5 ml) was added at room temperature and then, the mixture was refluxed for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/ethyl acetate=3/1) to obtain 195 mg (yield 56.5%) of the title compound.

Workup

  1. additiona mixture of IIa and IIb
  2. temperaturethe mixture was refluxed for 2 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography (a eluting solvent

Sources & evidence

ORD record
ord-7ff0bd5a30864223b43642abb58e8424
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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