Water → Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

4,6-Dichloronicotinic acid ethyl ester (43 g, 195 mmol) was dissolved in acetonitrile (600 mL), and cooled to 0° C., and then methylamine (125 mL of a 40% water solution, 977 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to rt over 3 h. Solvent was removed in vacuo and the crude product was purified using silica gel chromatography (1:1 hexanes/ethyl acetate eluant). The title compound was isolated as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.66 (s, 1H), 8.12 (bs, 1H), 6.53 (s, 1H), 4.34 (q, J=7.2 Hz, 2H), 2.92 (s, 3H), 1.37 (t, J=7.2 Hz, 3H).

Provenance & Evidence