Thionyl Chloride → 2,6-Dichlorpyridine-3-carbonyl chloride

HRID 1839365Notes

Reaction equation

HRID 1839365 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 122639842,6-Dichlorpyridine-3-carbonyl chloride

Procedure

A solution of commercially available (Aldrich) 2,6-dichloro-nicotinic acid (2.0 g, 10.4 mmol) in thionyl chloride (10 mL) was heated to 80° C. for 2 h. After cooling, the solution was concentrated in vacuo to give 2,6-dichloro-nicotinoyl chloride as yellow oil which was carried on to the next step without further purification. This transformation can also be accomplished using oxalyl chloride with catalytic DMF in place of thionyl chloride.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-535139919a434e10bb9ad21a485485b7
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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