Aniline → N-2-Pyridylaniline

Participants

Reaction Conditions

Reaction Steps

2-bromopyridine (3.0 g) and aniline (5.3 g) were dissolved in toluene (40 mL), tris(dibenzylideneacetone)dipalladium (0) (350 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (480 mg) and sodium tert-butoxide (2.6 g) were added, then stirred at 80° C. for three hours. Ethyl acetate (100 mL) was added to the reaction solution, and then washed with water (100 mL). The organic layer was extracted with 2N hydrochloric acid (100 mL), and washed with ethyl acetate (100 mL). The water layer was made alkaline with 2N sodium hydroxide aqueous solution (150 mL) and then extracted with ethyl acetate (200 mL). The organic layer was washed with a saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the residue was washed with diethyl ether to give the above-identified compound (2.1 g, yield 72%).

Provenance & Evidence