119165-69-4

16347-06-1

GENERAL METHOD: 2-(4,5-dihydro-1,3-oxazol-2-yl)pyridine (137 mg, 0.25 mmol) and pyridine (80 μL, 1.0 mmol) were dissolved in water (6 mL), followed by addition of pyridinium hydrobromide perbromide (320 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 23 h. The reaction mixture was then treated sequentially with 0.5 M Na2S2O3 aqueous solution (10 mL) and 1.0 M NaHCO3 aqueous solution (15 mL) and extracted with ethyl acetate (60 mL). The organic layer was washed with 0.5 M Na2S2O3 aqueous solution followed by saturated NaCl aqueous solution and dried with MgSO4. After evaporation of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (Wako C-200) using CCl4 and CCl4-CHCl3 (2:1 v/v) as eluents to afford N-(2-hydroxyethyl)-2-pyridinecarboxamide (38 mg, 0.23 mmol) in 92% yield.