Potassium Carbonate → 4-(trifluoromethyl)nicotinonitrile

HRID 1744277Notes

Reaction equation

HRID 1744277 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3](=O)[CH:4]=[CH:5][NH:6][CH:7]=[CH:8][C:9]#[N:10].C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CO>[C:9]([C:8]1[CH:7]=[N:6][CH:5]=[CH:4][C:3]=1[C:2]([F:13])([F:12])[F:1])#[N:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 731022503-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

Product 1

HCID 27367434-(trifluoromethyl)nicotinonitrileYield 32.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 1.90 g, 10 mmol) was dissolved in methanol (20 ml), and potassium carbonate (2.10 g, 15 mmol) was added. The mixture was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/ethyl acetate=3/1) to obtain 653 mg (yield 32.7%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (a eluting solvent

Sources & evidence

ORD record
ord-f47f2f6bbdd14935864e832b21b1afa8
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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