Triethylamine → 2-(Pivaloylamino)pyridine

Participants

Reaction Steps

To a solution of 2-aminopyridine (50.0 g, 531 mmol) in methylene chloride (500 mL) were added triethylamine (81.4 mL, 584 mmol) and pivaloyl chloride (71.9 mL, 584 mmol) at 0° C, which was stirred at room temperature for 4 hours 30 minutes. The reaction solution was partitioned in water and methylene chloride. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. To a solution of the resulting residue in methanol (300 mL) was added potassium carbonate (73.4 g, 531 mmol) at 0° C, which was stirred at room temperature for 90 minutes. The reaction solution was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. To the residue was added heptane (300 mL), and the deposited solid was recovered by filtration to obtain title compound (80.2 g). Furthermore, the filtrate was concentrated under a reduced pressure, the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (12.2 g).

Provenance & Evidence