Phosphorus pentachloride → 2-Chloro-5,6-dimethylpyridine-3-carbonitrile

HRID 224865Notes

Reaction equation

HRID 224865 reaction equation
[C:1]([C:3]1[C:4](O)=[N:5][C:6]([CH3:10])=[C:7]([CH3:9])[CH:8]=1)#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:13]>>[Cl:13][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([CH3:9])=[C:6]([CH3:10])[N:5]=1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178426619HCID 178426619, compound

Product 1

HCID 128911062-Chloro-5,6-dimethylpyridine-3-carbonitrileYield 53.6%

Procedure

An intimate mixture of 3-cyano-5,6-dimethyl-2-hydroxypyridine (42 g) and phosphorus pentachloride (81 g) was heated at 140°-160° for 2 hours. Phosphoryl chloride was removed by distillation under reduced pressure and icewater (500 g) was added to the residue. The mixture was adjusted to pH 7 with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to an oil which was crystallised from ether/petroleum ether (b.p. 60°-80°) to give 2-chloro-3-cyano-5,6-dimethylpyridine (25.3 g) m.p. 83°-87°.

Workup

  1. temperaturewas heated at 140°-160° for 2 hours
  2. customPhosphoryl chloride was removed by distillation under reduced pressure and icewater (500 g)
  3. additionwas added to the residue
  4. extractionextracted with ether
  5. customThe ether extracts were evaporated to an oil which
  6. customwas crystallised from ether/petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-657b84ad8eb94ca5b6c8b1e9a53c5a4c
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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