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 (40 mL). NaOH (3.3 eq., 118.5 mmol, 4.8 g) was added and the reaction heated to reflux for 16 hours. The volatiles were then removed from the cooled reaction medium, and the pH adjusted to precisely pH 7.0 with 3.0 M HCl. The solvent was removed and the residue slurried in boiling methanol, filtered whilst hot, and the filtrate evaporated to dryness. This crude product contains residual free morpholine, which was removed by flash column chromatography, eluting with 9:1 EtOAc/MeOH. The fractions were analysed by TLC eluting with 1:1 EtOAc/MeOH (Rf=0.209). The product was obtained in 46% yield.

Provenance & Evidence