Phosphorus oxychloride → 2-Chloro-5-(chloromethyl)pyridine

HRID 483346Notes

Reaction equation

HRID 483346 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][Cl:12])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 24819Phosphorus pentachlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridineYield 108.6%

Conditions

Temperature
120 °C

Procedure

6-Chloronicotinic acid (23.36 g, 0.18 mol), phosphorus pentachloride (41.65 g, 0.20 mol) and phosphorus oxychloride (20.50 ml, 0.22 mol) were stirred vigorously together at ambient temperature (20° C.). The resulting mixture was heated with stirring to 120° C. and kept at that temperature for a further 3 hours. The mixture was then allowed to cool to ambient temperature (20° C.) and excess phosphorus oxychloride was evaporated off under reduced pressure to yield 6-chloronicotinyl chloride as a brown oil 31.68 g, 100%), which was used directly in the following step.

Workup

  1. temperatureThe resulting mixture was heated
  2. customwas evaporated off under reduced pressure

Sources & evidence

ORD record
ord-27a31a55ff254ec3915f6c673effdb87
Source dataset
uspto-grants-1993_07
Patent number
US05225423

Reaction notes

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