1,6-Naphthyridine → 1,2,3,4-Tetrahydro-1,8-naphthyridine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 0.8315 g (6.39 mmol) 1,6-naphthyridine in 25 mL EtOH was added 0.0875 g Pd (10% on C). The reaction mixture was stirred under H2 at atmospheric pressure. After 24 h, an additional 0.0431 g Pd (10% on C) was added. After a total of 46 h under H2 at atmospheric pressure, the reaction mixture was diluted with 50 mL EtOH and filtered over celite. The celite was washed with 300 mL EtOH, and the filtrate concentrated in vacuo. Purification by flash chromatography (50×105 mm silica gel, linear gradient 5-10% (10% NH4H:MeOH):CH2Cl2) yielded 32. 1H NMR (CDCl3, 400 MHz) δ 7.969 (d, 2H, J=4.94 Hz, ArH); 6.279 (d, 1H, J=5.57 Hz, ArH); 3.361-3.326 (m, 2H, CH2); 2.703 (t, 2H, J=6.27 Hz, CH2); 1.962-1.903 (m, 2H, CH2); MS (Electrospray): m/z 134.9 (M+H).

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