Water → 2-(Pivaloylamino)pyridine

Participants

Reaction Conditions

Reaction Steps

2-Aminopyridine (14.1 g) and triethylamine (19.0 g) were dissolved in dichloromethane (200 ml) to prepare a solution which was cooled to 0° C. A solution of pivaloyl chloride (19.9 g) in dichloromethane (30 ml) was gradually added dropwise thereto, and the mixture was stirred at 0° C. for 15 min. Thereafter, the reaction solution was stirred at room temperature for 4 hr. The reaction solution was poured into water (150 ml), and the dichloromethane layer was washed with a dilute aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform to give 2,2-dimethyl-N-pyridin-2-yl-propionamide (25.2 g, yield 95%).

Provenance & Evidence