33402-75-4

67-56-1

3222-50-2

33402-75-4

4-Methylpyridine-3-carboxylic acid (2.00 g, 14.6 mmol) was dissolved in methanol (50 mL) and concentrated sulfuric acid (4.66 mL, 87.6 mmol) was added. The reaction mixture was stirred at 60 °C for 16 hours. After the reaction was completed, it was concentrated under reduced pressure to remove most of the methanol. The concentrated mixture was extracted by partitioning with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate (200 mL). The organic layer was separated, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to constant weight to give methyl 4-methylnicotinate as a clear liquid (2.30 g, 94% yield).LC/MS analysis (conditions are given in Table 2, Method a) showed a retention time of Rt = 1.67 min; mass spectrum m/z: 152 ([M+H]+).