4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine

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Reaction Steps

A portion (4.9 g) of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime obtained in Step 1 was suspended in methanol (50 mL) and acetic acid (25 mL), followed by stirring at room temperature for 18 hrs under a hydrogen atmosphere in the presence of 10% palladium-carbon (0.5 g). The insoluble matter was separated by filtration with Celite® pad and the filtrate was concentrated; thereafter, the residue was dissolved in water and the pH of the solution was adjusted to about 8 with sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate; the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol) to yield the titled compound as pale yellow crystals (4.0 g).

Provenance & Evidence