Aniline → HCID 110176454, compound

Participants

Reaction Conditions

Reaction Steps

SODIUM TERT-BUTOXIDE (0.984 g, 10.24 mmol) was added to 2,6-dichloro-N- methylisonicotinamide (1.5 g, 7.32 mmol), ANILINE (0.667 mL, 7.32 mmol), PALLADIUM(II) ACETATE (0.016 g, 0.07 mmol) and XANTPHOS (0.127 g, 0.22 mmol) in toluene (30 mL) under nitrogen. The resulting mixture was stirred at 80 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with water (2 x 50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 30 to 80% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 2-chloro-N- methyl-6-(phenylamino)isonicotinamide (1.012 g, 52.9 %) as a cream solid.

Provenance & Evidence