Thionyl Chloride → 2,6-Dichloro-4-methylnicotinoyl chloride

HRID 1839355Notes

Reaction equation

HRID 1839355 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([Cl:15])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 219482142,6-Dichloro-4-methylnicotinoyl chloride

Procedure

A solution of 2,6-dichloro-4-methyl-nicotinic acid (3.94 g, 19.1 mmol) in thionyl chloride (18 mL) was heated to 80° C. for 2 h. After cooling, the solution was concentrated in vacuo to give 2,6-dichloro-4-methyl-nicotinoyl chloride as yellow oil. It 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-d9c9307264ee4dae82a8ef60d5afc6c3
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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