Thionyl Chloride → 2-Chloropyridine-4-carbonyl chloride

HRID 602423Notes

Reaction equation

HRID 602423 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([Cl:13])=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 28000032-Chloropyridine-4-carbonyl chloride

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-isonicotinic acid (15 g, 95.2 mmol) and thionyl chloride (90 mL) was heated at 100° C. After completion of the reaction the mixture was concentrated in vacuo. Residual thionyl chloride was removed by azeotropic distillation with toluene, to give 2-chloro-isonicotinoyl chloride (15.33 g).

Workup

  1. customAfter completion of the reaction the mixture
  2. concentrationwas concentrated in vacuo
  3. customResidual thionyl chloride was removed by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-33dacb30542846ac97f74512707fb5e8
Source dataset
uspto-grants-2011_03
Patent number
US07906533B2

Reaction notes

Loading…