Water → 5-Methyl-6-(2-methylpyrrolidin-1-yl)nicotinic acid

Participants

Reaction Steps

A solution of 5-methyl-6-(2-methylpyrrolidin-1-yl)nicotinonitrile obtained in step 1 (591 mg; 2.94 mmol) in water (15 mL) and KOH (823 mg; 14.68 mmol) was heated at reflux for 16 hours. Reaction mixture was basified to pH 6 and extracted with EtOAc to give the title compound as a white solid. 1H NMR (DMSO-d6) δ 12.43 (s, 1H), 8.48 (d, J=2.2 Hz, 1H), 7.74-7.73 (m, 1H), 4.41-4.32 (m, 1H), 3.81-3.73 (m, 1H), 3.49-3.42 (m, 1H), 2.29 (s, 3H), 2.10-2.04 (m, 1H), 1.94-1.88 (m, 1H), 1.74-1.68 (m, 1H), 1.59-1.52 (m, 1H), 1.25 (d, J=6 Hz, 3H). HPLC (Method A) Rt 1.45 min (Purity: 99.8%). LC/MS (Method B): 221.2 (M+H)+.

Provenance & Evidence