Aniline → N-phenylpyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

ANILINE (1.730 mL, 18.99 mmol) was added to 4-bromopyridine (2.5 g, 15.82 mmol), PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol), XANTPHOS (0.549 g, 0.95 mmol) and SODIUM TERT-BUTOXIDE (2.129 g, 22.15 mmol) in toluene (125 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 (100 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 (1.102 g, 40.9 %) as a white solid.

Provenance & Evidence