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

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Reaction Steps

6-Benzyl-5,6,7,8-tetrahydro-[1,6]naphthyridine (3.10 g, 13.82 mmol) is dissolved in acetic acid (40 ml). To the solution is added Pd—C (10%, 500 mg). The resulting mixture is hydrogenated under 40-50 psi at 55-60° C. for 10 hr. The solid catalyst is removed by filtration, and the filtering cake is washed with MeOH (20 ml×2). The combined organic phase is evaporated to dryness. The residue is taken up into water (25.0 ml), basified with saturated sodium carbonate solution, and extracted with EtOAc (30 ml×3). The combined organic phase is dried with sodium sulfate, and concentrated to give the title compound. MS (+VE) m/z 135.1 (M++1).

Provenance & Evidence