Aniline → N-phenylpyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

ANILINE (3.94 mL, 43.29 mmol) was added to 4-bromopyridine (5.7 g, 36.08 mmol), PALLADIUM(II) ACETATE (0.162 g, 0.72 mmol), XANTPHOS (1.252 g, 2.16 mmol) and SODIUM TERT-BUTOXIDE (4.85 g, 50.51 mmol) in toluene (280 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (200 mL), and washed sequentially with water (2 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford N-phenylpyridin-4-amine (1.528 g, 24.88 %) as a pink solid.

Provenance & Evidence