1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(phenylmethyl)- → 5,6,7,8-Tetrahydro-1,6-naphthyridine

Participants

Reaction Steps

6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine (5.0 g, 22.3 mmol) was dissolved in acetic acid (150 ml) and treated with 10% palladium on carbon (2.5 g). The reaction mixture was subjected to 40 psig hydrogen at 55° on a Parr hydrogenation apparatus for 18 hours; the mixture was then filtered through Super-Cel. The filtrate was evaporated to an amber oil, which was dissolved in 6N sodium hydroxide solution and extracted with toluene (2×50 ml) and methylene chloride (2×50 ml). The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to provide the title product as a light amber oil (2.8 g, 21 mmol, 94% yield).

Provenance & Evidence