4-methyl-N-(alpha-phenylethyl)phenoxazine → 4-Methyl-10H-phenoxazine

Participants

Reaction Steps

4-methyl-N-(α-phenylethyl)phenoxazine in 30 ml of ethyl acetate and 130 ml of ethanol was hydrogenated at atmospheric pressure (585 mm Hg) in the presence of 1.5 g of 10% palladium-charcoal as catalyst, until the calculated amount of hydrogen was consumed (16 hours). The catalyst was then separated by filtration through celite and the solvent removed under reduced pressure. Chromatography of the solid residue (1 g) on 100 g of silica gel in a column, using hexane-ethyl acetate (80:20) as the eluting solvent produced 4-methylphenoxazine, a white solid, which was recrystallized from pentane, mp: 91° C.

Provenance & Evidence