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

Participants

Reaction Steps

2-Methylpyridin-3-ol (3.00 g, 27.5 mmol) was dissolved in a solution of Na2CO3 (5.83 g, 55.0 mmol) in water (48 mL) and MeOH (30 mL). Iodine (6.98 g, 27.5 mmol) was added and the reaction mixture was stirred for 1 h at RT. The mixture was treated with 2 M HCl solution (14 mL) and the resultant suspension was extracted with EtOAc (2×65 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was slurried with DCM (20 mL) and the resultant solid was collected to afford 6-iodo-2-methylpyridin-3-ol (3.6 g, 55.7% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.41 (d, J=8.26 Hz, 1H), 6.78 (d, J=8.26 Hz, 1H), 5.03 (br s, 1H), 2.47 (s, 3H); MS (ESI) m/z: 236.0 (M+H+).

Provenance & Evidence