Thionyl Chloride → 6-Chloronicotinoyl Chloride

HRID 1080690Notes

Reaction equation

HRID 1080690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([Cl:13])=[O:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acid

Product 1

HCID 27821656-Chloronicotinoyl Chloride

Procedure

2-Chloropyridine-5-carboxylic acid (25 g) was dissolved in thionyl chloride (200 mL) and the mixture was heated at reflux for 24 hours. The excess thionyl chloride was removed by distillation at atmospheric pressure and the residue was distilled under reduced pressure to yield the titled compound as a clear oil (26.4 g) having a boiling point of 128°-130° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe excess thionyl chloride was removed by distillation at atmospheric pressure
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2acfcd6e949c4ab99632fa2a28135741
Source dataset
uspto-grants-1996_12
Patent number
US05583148

Reaction notes

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