Water → 4-Chloro-2-pyridinecarbonitrile

HRID 971655Notes

Reaction equation

HRID 971655 reaction equation
[C:1]([C:3]1[CH:8]=[C:7](CO)[CH:6]=[CH:5][N:4]=1)#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:12].O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[C:7]([Cl:12])[CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 6933424-Chloro-2-pyridinecarbonitrileYield 91.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a magnetically stirred solution of 9 grams (66 mm) of 2-cyano-4-hydroxymethylpyridine [Swan, et al. J. Chem. Soc., 3440 (1963)] contained in 300 mls of benzene is added 15.1 grams (72 mm) of phosphorous pentachloride. After stirring for 1/2 hour, ice and water are added followed by sodium bicarbonate. The organic layer is washed with water and evaporated. The residual oil is crystallized from petroleum ether, to yield 8.5 grams (83%) of 2-cyano-4-pyridyl chloride, m.p. -55°-56°.

Workup

  1. washThe organic layer is washed with water
  2. customevaporated
  3. customThe residual oil is crystallized from petroleum ether

Sources & evidence

ORD record
ord-f137f82ac81f4bc4ab0f67d046d3c0fb
Source dataset
uspto-grants-1979_07
Patent number
US04160835

Reaction notes

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