Sulfuric Acid → 2-methylquinoline-7-carboxylic Acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-7-(trifluoromethyl)quinoline (5.2 g, 24.6 mmol) and 80% H2SO4 (18.1 g, 148 mmol) was heated at 230° C. for 20 minutes. After cooling to ambient temperature, the mixture was basified by 6 N NaOH to about pH 12. The resulting solid was removed by filtration. The filtrate was acidified by 2 N HCl to about pH 3, extracted with 3:1 DCM/IPA (2×50 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure to give 2-methylquinoline-7-carboxylic acid (3.3 g, 71.6%) as a solid.

Provenance & Evidence