Hydrochloric Acid → 2-Methyl-3-hydroxy-6-iodopyridine

Participants

Reaction Steps

To a suspension of 1.05 g (9.62 mmol) of 2-methyl-3-hydroxypyridine and 2.04 g (19.24 mmol) of sodium carbonate in 10 mL of H2O and 5 mL of CH3OH was added 2.44 g (9.62 mmol) of iodine in several portions. After stirring at rt for 30 min, the reaction mixture was acidified using 5.0 N HCl until pH=3. The mixture was extracted with EtOAc (3×20 mL). Organic layers were combined, dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded 1.04 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.28 (s, 3H), 6.76 (d, J=8.2, 1H), 7.34 (d, J=8.7, 1H).

Provenance & Evidence