Synthesis
General procedure for the synthesis of 5,6,7,8-tetrahydro-8-aminoquinolines from 6,7-dihydroquinolin-8(5H)-one oxime: 6,7-dihydro-8(5H)-quinolinone oxime (0.50 g, 3.1 mmol) was dissolved in 35 mL of methanol and 50 mg 10% Pd/C catalyst was added. The catalytic hydrogenation reaction was carried out at 50 psi hydrogen pressure. After 18 hours of reaction, the hydrogen in the reaction system was replaced with nitrogen and the reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated to dryness under reduced pressure to give 0.42 g (92% yield) of 5,6,7,8-tetrahydro-8-aminoquinoline as a purple oil.1H NMR (CDCl3) δ: 8.39 (d, 1H), 7.36 (d, 1H), 7.04 (m, 1H), 4.00 (t, 1H), 2.88-2.67 (m, 2H), 2.18 (m, 1H), 2.03-1.62 (m, 5H).
References
[1] Patent: WO2006/20415, 2006, A1. Location in patent: Page/Page column 112
[2] Synthetic Communications, 2003, vol. 33, # 20, p. 3497 - 3502
[3] Organic Process Research and Development, 2008, vol. 12, # 5, p. 823 - 830
[4] Chemical Communications, 2016, vol. 52, # 38, p. 6423 - 6426
