Dichloromethane → 2-(Pivaloylamino)pyridine

Participants

Reaction Steps

To a methylene chloride (500 mL) solution of 2-aminopyridine (50 g) were added triethylamine (81 mL) and pivaloyl chloride (72 mL) at 0° C., which was stirred for 4 hours and 30 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with methylene chloride. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under a reduced pressure. Potassium carbonate (73 g) was added at 0° C. to a methanol (300 mL) solution of the residue thus obtained, which was stirred for 90 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was concentrated under a reduced pressure. Heptane (300 mL) was added to the residue, and the precipitated solids were filtered off to obtain the titled compound (80 g). The filtrate was then further concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (12 g).

Provenance & Evidence