Water → 2-Cyano-6-fluoro-3-nitropyridine

HRID 50763Notes

Reaction equation

HRID 50763 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[F-:13].[K+].O>CC#N>[C:8]([C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=[C:2]([F:13])[N:7]=1)#[N:9]

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 108448072-Cyano-6-fluoro-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-2-cyano-3-nitropyridine [Colbry, N. L.; Elslager, E. F. ; Werbel, L. M.; J. Het. Chem., 1984, 21, 1521-1525] (10.0 g, 0.054 mol) and KF (9.48 g, 0.163 mol) in MeCN (200 mL) is heated under reflux with stirring for 18 h, then poured into water and extracted with EtOAc. The extract is washed with water and worked up, and the residue is chromatographed on silica gel, eluting with EtOAc/petroleum ether (3:7), to give after removal of the solvent under reduced pressure 2-cyano-6-fluoro-3-nitropyridine (7.2 g, 79%). 1H NMR (CDCl3) δ 8.79 (1H, dd, J=9.0, 6.0 Hz), 7.48 (1H, dd, J=9.0, 3.0 Hz).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. extractionextracted with EtOAc
  4. washThe extract is washed with water
  5. customthe residue is chromatographed on silica gel
  6. washeluting with EtOAc/petroleum ether (3:7)
  7. customto give
  8. customafter removal of the solvent under reduced pressure 2-cyano-6-fluoro-3-nitropyridine (7.2 g, 79%)

Sources & evidence

ORD record
ord-78540ebc428a4cc1aeac315755fbace5
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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