Hydrochloric Acid → 4-Propylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-propylpyridine (10.0 g, 82.5 mmol) in toluene (170 mL), sodium amide (6.4 g, 165 mmol) was added at room temperature, and the mixture was stirred at 140° C. for 2 days. Under ice-cold conditions, the reaction solution was added 6N aqueous solution of hydrochloric acid (30 mL), and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate/1% triethylamine), and the title compound (5.70 g (yield 51%)) was obtained as a red-brown solid.

Provenance & Evidence