Thionyl Chloride → 3-Methylpyridine-4-carbonyl chloride--hydrogen chloride (1/1)

HRID 441188Notes

Reaction equation

HRID 441188 reaction equation
[CH3:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[ClH:13].[CH3:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15020033-Methyl-isonicotinic acid

Product 1

HCID 224055433-Methylpyridine-4-carbonyl chloride--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-methylisonicotinic acid (0.676 g) in toluene was added thionyl chloride (0.5 mL), and the reaction mixture was heated under reflux 70 min. The resulting solution was decanted from a gummy residue on the bottom of the reaction flask, evaporated and further dried under high vacuum to afford 3-methylisonicotinoyl chloride hydrochloride which was used for the acylation without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux 70 min
  3. customThe resulting solution was decanted from a gummy residue on the bottom of the reaction flask
  4. customevaporated
  5. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-a0022676a5f541b0869082e719c8240b
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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