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

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])=[O:4].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([Cl:16])=[O:8])=[O:4]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 986262-Methyl 2,3-pyridinedicarboxylate

Product 1

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

Procedure

A mixture of 2-methoxycarbonylnicotinic acid (4.0 g) and thionyl chloride (30 ml) is heated under reflux until homogeneous. The remaining thionyl chloride is distilled off in vacuo to give 2-methoxycarbonylnicotinoyl chloride.

Workup

temperatureis heated
temperatureunder reflux until homogeneous
distillationThe remaining thionyl chloride is distilled off in vacuo

Sources & evidence

ORD record: ord-0a674054ae48429ca299facb44bdd7ba
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098462

Reaction notes

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