Thionyl Chloride → 2-Pyridinecarboxylic acid, 3-(chlorocarbonyl)-, methyl ester

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

Reactant 2

HCID 24386Thionyl Chloride

HCID 986262-Methyl 2,3-pyridinedicarboxylate

Product 1

HCID 132396602-Pyridinecarboxylic acid, 3-(chlorocarbonyl)-, methyl esterYield 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

temperatureheated
temperatureto reflux for 4 h
customExcess thionyl chloride was removed under vacuum

Sources & evidence

ORD record: ord-7fdcd6ce251842918e4673b775f75561
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410117B2

Reaction notes

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