5,7-diethyl-[1,6]naphthyridin-2(1H)-one → 5,7-diethyl-3,4-dihydro-1,6-naphthyridin-2(1H)-one

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Reaction Steps

A solution of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (10.0 g) in ethanol (100 ml) was catalytically hydrogenated over 10% palladium on carbon (1 g) at 50° C. and a pressure of 20 atmospheres for 30 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated under vacuum to give 5,7-diethyl-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one (9.6 g), m.p. 90°-94° C.; NMR: 1.2-1.3(m, 6H), 2.6-2.85(m, 6H), 3.05(t, 2H), 6.5(s, 1H), 8.9(br s, 1H).

Provenance & Evidence