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

HRID 2214982Notes

Reaction equation

HRID 2214982 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-e3983e3b687446b7ade8e3a483c11209
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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