Cyclopentanone → 2-amino-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

Participants

Reaction Steps

In 12 ml of toluene, 500 mg (5.94 mmol) of cyclopentanone, 916 mg (5.94 mmol) of benzylidenemalononitrile and 1.00 g (13.1 mmol) of ammonium acetate were heated under reflux for 2 h. The mixture was washed with 10 ml of a saturated aqueous sodium bicarbonate solution and then with 10 ml of water, dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Provenance & Evidence