Phosphorus pentachloride → 3-Chloropyridine-2-carbonitrile

HRID 1939894Notes

Reaction equation

HRID 1939894 reaction equation
O[C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12]>P(Cl)(Cl)(Cl)=O>[Cl:12][C:2]1[C:3]([C:8]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 702773-Hydroxypicolinamide

Product 1

HCID 8182583-Chloropyridine-2-carbonitrileYield 14.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of 3-hydroxypicolinamide (2.00 g, 14.5 mmol) in phosphorus oxychloride (10 mL) at room temperature was added phosphorus pentachloride (6.00 g, 28.8 mmol). The mixture was heated at reflux for 90 min, and the solvent was removed by distillation. The residue was poured into water, the aqueous solution was neutralized by addition of sodium bicarbonate, and was extracted with ethyl acetate. The organic phase was filtered through silica gel, the filtrate was concentrated, and the residue was subjected to flash chromatography on silica gel, affording 300 mg of 3-chloro-2-cyanopyridine. 1H NMR (CDCl3) δ7.50 (dd, 1, J=4.8, 8.4), 7.89 (dd, 1, J=1.6, 8.4), 8.63 (dd, 1, J=1.6, 4.8).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 min
  3. customthe solvent was removed by distillation
  4. additionThe residue was poured into water
  5. additionthe aqueous solution was neutralized by addition of sodium bicarbonate
  6. extractionwas extracted with ethyl acetate
  7. filtrationThe organic phase was filtered through silica gel
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-551c5a8a785344a79ea5476401638107
Source dataset
uspto-grants-1997_12
Patent number
US05698547

Reaction notes

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