Water → 4-(trifluoromethyl)nicotinonitrile

HRID 1744271Notes

Reaction equation

HRID 1744271 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 47.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 28% sodium methoxide (290 mg, 1.5 mmol), a solution prepared by dissolving 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a high-polar compound IIb; 190 mg, 1.0 mmol) in methanol (2 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 thin layer chromatography (a developing solvent: hexane/ethyl acetate=3/1) to obtain 81.0 mg (yield 47.2%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by thin layer chromatography (a developing solvent

Sources & evidence

ORD record
ord-6c5aa1c0b881416080dcb7f41377bb50
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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