GENERAL METHOD: In a dry Schlenk tube, 2-bromo-3-methylpyridine (5.98 g, 35.0 mmol) was dissolved in 100 mL of ammonia (Am-OH) and potassium tert-butanol (KOt-Bu, 39.3 g, 350.0 mmol) was added. The reaction mixture was stirred at 100 °C for 40 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 50 mL of formic acid (HCO2H) and stirred at room temperature for 24 hours. Subsequently, the pH was adjusted to about 6 using 3N aqueous potassium hydroxide (KOH). extraction was carried out with chloroform (CHCl3, 3 x 50 mL), the organic phases were combined and washed with saturated saline, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (eluent: 8% methanol/dichloromethane) to afford the target product 2-hydroxy-3-methylpyridine (1) as a white solid with a yield of 2.75 g in 72% yield.
