Sodium Hydroxide → (6-Methylpyridin-3-yl)acetic acid

Participants

Reaction Steps

Crude 2-(6-Methyl-pyridin-3-yl)-1-morpholin-4-yl-ethanethione (39.5 mmol, 9.685 g) was suspended in 2:1 H2O/EtOH (75 cm3). NaOH (3.3 eq., 118.5 mmol, 4.8 g) added and the reaction heated to reflux for 16 hours. Volatiles were then removed from the cooled reaction medium, and the aqueous residue extracted with DCM (3×50 cm3). The pH was adjusted to precisely pH 7.0 with HCl, and a further DCM extraction performed (3×50 cm3). Water was removed from the residue, and the obtained solids slurried in methanol, filtered, and the filtrate evaporated to dryness. The orange solid obtained gave spectroscopic data consistent with the desired product. Mass recovery is typically >100% however this is due to NaCl within the product.

Provenance & Evidence