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

Participants

Reaction Steps

A solution of 5-methyl-6-(2-methylpiperidin-1-yl)nicotinonitrile obtained in step 1 (1.0 g; 4.64 mmol) and KOH (1.3 g; 23.22 mmol) in water (60 mL) was heated at reflux for 16 hours. After this time, reaction mixture was acidified to pH 3 and extracted with EtOAc to give the title compound as a yellow solid (1.1 g, quantitative). 1H NMR (DMSO-d6) δ 12.82 (bs, 1H), 8.58 (d, J=2.3 Hz, 1H), 7.88 (d, J=2.3 Hz, 1H), 3.85-3.82 (m, 1H), 3.19-3.10 (m, 2H), 2.24 (s, 3H), 1.75-1.44 (m, 6H), 1.04 (d, J=6.2 Hz, 3H). HPLC (Method B) Rt 1.96 min (Purity: 92.2%). LC/MS (Method A): 235.2 (M+H)+.

Provenance & Evidence