1,8-Naphthyridine, 2-methyl- → 7-Methyl-1,2,3,4-tetrahydro-1,8-naphthyridine

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Reaction Steps

A mixture of 2-methyl-1,8-naphthyridine (18.5 g, 128 mmole), 10% Pd/C (5 g), and absolute EtOH (150 mL) was shaken under hydrogen (15 psi) on a Parr apparatus. After 24 hr, the mixture was filtered through celite®, and the filter pad was washed sequentially with absolute EtOH and EtOAc. The filtrate was concentrated to dryness to leave the title compound (18.85 g, 99%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.02 (d, J=7.5 Hz, 1H), 6.34 (d, J=7.5 Hz, 1 H), 4.80 (br s, 1 H), 3.38 (m, 2H), 2.74 (m, 2H), 2.30 (s, 3H), 1.88 (m, 2H); MS (ES) m/e 149 (M+H)+.

Provenance & Evidence