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

HRID 2214992Notes

Reaction equation

HRID 2214992 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-6a07647e513444f6bf1341303a378f0a
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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