Sodium hydroxide ethanol → 5-Trifluoromethyl-6-(morpholin-4-yl)-nicotinic acid

Participants

Reaction Steps

A solution of 249 mg (0.97 mmol) of 2-(morpholin-4-yl)-3-trifluoromethyl-5-cyanopyridine (from Step D) in 5 mL 1:1 v/v 5 N NaOH/EtOH was heated at reflux for 1 h. The mixture was cooled and partitioned between 20 mL of ether and 20 mL of water. The aqueous layer was separated and adjusted to pH=4 with conc. HCl. The precipitated solid was filtered, rinsed with water and dried to afford 138 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 3.52 (app t, J=5.0, 4H), 3.78 (app t, J=5.0, 4H), 8.40 (d, J=2.0, 1H), 8.90 (d, J=2.0, 1H); ESI-MS (m/z) 277.3; HPLC A: 2.71 min.

Provenance & Evidence