Thionyl Chloride → 2-Chloropyridine-4-carbonyl chloride

HRID 1080686Notes

Reaction equation

HRID 1080686 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([Cl:13])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 28000032-Chloropyridine-4-carbonyl chloride

Procedure

A solution of 2-chloropyridine-4-carboxylic acid (10 g) in thionyl chloride (90 mL) was heated under reflux for 20 hours. The excess thionyl chloride was removed by distillation at atmospheric pressure and the oily residue was distilled to give 9.26 grams of 2-chloropyridine-4-carbonyl chloride having a boiling point of 144°-148° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe excess thionyl chloride was removed by distillation at atmospheric pressure
  3. distillationthe oily residue was distilled

Sources & evidence

ORD record
ord-0be045e21a9b4efa84f877d272d54d19
Source dataset
uspto-grants-1996_12
Patent number
US05583148

Reaction notes

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