Potassium Fluoride → 2-Cyano-3-fluoropyridine

HRID 431853Notes

Reaction equation

HRID 431853 reaction equation
[C:1]([C:3]1[C:8](Cl)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[F-:10].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[C:1]([C:3]1[C:8]([F:10])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 8182583-Chloropyridine-2-carbonitrile

Product 1

HCID 70604082-Cyano-3-fluoropyridineYield 50.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-cyano-3-chloropyridine (1 g, 7.22 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was treated with potassium fluoride (1.26 g, 21.68 mmol) and heated at reflux for 18 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. Silica gel chromatography afforded 442 mg (50%) of 2-cyano-3-fluoropyridine.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. extractionextracted with water and brine

Sources & evidence

ORD record
ord-014da495d5b5402d8cbd5806a0c66b61
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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