Phosphorus pentachloride → 3-Chloropyridine-2-carbonitrile

HRID 1451217Notes

Reaction equation

HRID 1451217 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=l.6, 8.4), 8.63 (dd, 1, J=l.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-819ce5a4f0b6481bb3c42ac5cb8b7578
Source dataset
uspto-grants-1997_02
Patent number
US05604218

Reaction notes

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