Lithium Hydroxide → 6-(3-Cyanophenyl)nicotinic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-(3-cyanophenyl)nicotinate (300 mg, 1.26 mmol) and 2 M lithium hydroxide solution (1.89 mL) in tetrahydrofuran (30 mL) was heated at 40° C. overnight. The tetrahydrofuran was evaporated off, water (5 mL) was added and the reaction mixture was acidified to pH 6 with 2N aqueous HCl. The precipitated solid was filtered off and dried under vacuum to give 6-(3-cyanophenyl)nicotinic acid (208 mg). 1H NMR (400 MHz, DMSO-d6) ppm 7.74 (t, J=7.8 Hz, 1H), 7.96 (m, 1H), 8.23 (m, 1H), 8.36 (m, 1H), 8.49 (m, 1H), 8.55 (m, 1H), 9.15 (m, 1H), 13.5 (broad s, 1H) LCMS 225 (M+1) ELSD 1.33 minutes.

Provenance & Evidence