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

HRID 1063519Notes

Reaction equation

HRID 1063519 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-35fedcea2ad943c78314102c0dfea42a
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

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