Hydrochloric Acid → 2-Chloro-5-fluoronicotinic acid

Participants

Reaction Steps

Ethyl-2-chloro-5-fluoro-nicotinoate (50.4 g, 0.247 mol) (J. Med. Chem., 1993, 36(18), 2676–88) was dissolved in tetrahydrofuran (350 mL) and a 2M aqueous solution of lithium hydroxide (247 mL, 0.495 mol) added. The reaction mixture was stirred at room temperature for 3 days. The pH of the solution was reduced to pH1 by addition of 6M hydrochloric acid and then extracted with dichloromethane (x3). The combined extracts were dried over magnesium sulphate and the solvent concentrated in vacuo to give a solid which was triturated with diethyl ether and then dried to give the title compound as a white solid, 40.56 g.

Provenance & Evidence