Potassium Fluoride → 2-Cyano-5-fluoropyridine

HRID 431845Notes

Reaction equation

HRID 431845 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](Cl)=[CH:5][N:4]=1)#[N:2].[F-:10].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:10])=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 38339425-Chloro-2-cyanopyridine

Product 1

HCID 113324532-Cyano-5-fluoropyridineYield 48.2%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 2-cyano-5-chloropyridine (1 g, 7.22 mmol) and potassium fluoride (1.26 g, 21.68 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was heated at reflux for 18 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. The organic solvents were then removed in vacuo. Silica gel chromatography of the residue afforded 425 mg (48%) of 2-cyano-5-fluoropyridine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. extractionextracted with water and brine
  5. customThe organic solvents were then removed in vacuo

Sources & evidence

ORD record
ord-b3b49210dfa7459197c3746029572f17
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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