Acetonitrile → 2-(2-(2-Picolyl)aminoanilin-5-yl)benzoxazole

Participants

Reaction Steps

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (500 mg, 1.9 mmol) was added to an acetonitrile (5 mL) suspension containing 2-picolylamine (520 mg, 4.8 mmol), and this was heated to reflux for 2.5 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (7 mL) of the crystals obtained was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 14 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (480 mg, 78% yield) as a white solid.

Provenance & Evidence