Toluene → 5-Chloro-3-methylpicolinoyl chloride

HRID 1772170Notes

Reaction equation

HRID 1772170 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH3:15])[C:9]([C:12](O)=[O:13])=[N:10][CH:11]=1.C1(C)C=CC=CC=1>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH3:15])[C:9]([C:12]([Cl:3])=[O:13])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 223920095-Chloro-3-methylpyridine-2-carboxylic acid

Product 1

HCID 1179025195-Chloro-3-methylpicolinoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (71 μl, 962 μmol) is added to a mixture of 5-chloro-3-methyl-pyridine-2-carboxylic acid (150 mg, 874 μmol), toluene (1 ml) and DMF (20 μl). The mixture is heated to 60° C. for 1 hour. The mixture is concentrated in vacuo and the crude product used directly without further purification.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe crude product used directly without further purification

Sources & evidence

ORD record
ord-bbaeffbbde1f46399a97d7b1c1057c54
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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