Reaction #71665

ord-28888c9382e4446bb381c41c5071db41

Reaction equation

Cc1ncccc1C(=O)O
2-methyl-3-pyridinecarboxylic acid
O=S(Cl)Cl
thionyl chloride
Cc1ncccc1C(=O)Cl
title compound
Yield 100.0%
Cc1ncccc1C(=O)Cl
2-methyl-3-pyridinecarbonyl chloride
Yield 100.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction was concentrated under reduced pressure

Procedure

2-methyl-3-pyridinecarboxylic acid (20 g, 146 mmol) was dissolved in thionyl chloride (60 ml, 822 mmol) and stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure, to obtain the title compound as a white solid (28.1 g, 146 mmol). Acyl chloride was checked by quenching a sample in MeOH, LCMS showed methyl ester derivative. {[M+H]+=152}

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536183B2uspto-grants-2013_09