Thionyl Chloride → Methyl 3-(chlorocarbonyl)pyridine-2-carboxylate

HRID 1958325Notes

Reaction equation

HRID 1958325 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([Cl:16])=[O:13])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 98626Quinolinic acid, 2-methyl ester

Product 1

HCID 13239660Methyl 3-(chlorocarbonyl)pyridine-2-carboxylateYield 112.5%

Procedure

Pyridine-2,3-dicarboxylic acid 2-methyl ester (500 mg, 2.76 mmol) was dissolved in thionyl chloride (8.21 g, 68 mmol) and heated to reflux for 4 h. Excess thionyl chloride was removed under vacuum. The obtained crude product (620 mg, assumed purity 60%, 68% yield) was used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customExcess thionyl chloride was removed under vacuum

Sources & evidence

ORD record
ord-7fdcd6ce251842918e4673b775f75561
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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