Hydrochloric Acid → 2-Chloro-4-methylpyridine-3-carboxylic acid

Participants

Reaction Steps

A mixture of 21.8 g (0.109 mole) of ethyl 2-chloro-4-methyl-nicotinate (6) and 55 mL of a 2N-sodium hydroxide solution in 20 mL of ethanol, was refluxed for 8 hours. The solution was acidified with 2N hydrochloric acid and extracted with ether. The organic phase was dried over magnesium sulfate, filtered and concentrated to give 14.8 g (79%) of 2-chloro-4-methylnicotinic acid (7)- as a white solid, mp: 152-154° C., MS (MH)+ 172, NMR (DMSO) ppm: 2.34 (s,3H); 7.39 (d,1H); 8.33 (d,1H); 14.0 (bs COOH).

Provenance & Evidence