In-Situ Liquid Phase Catalytic Hydrogenation for One-Pot Synthesis of Quinolines from Aromatic Nitro Compounds

doi:10.3724/SP.J.1088.2012.20341

Abstract

Abstract: A new hydrogenation system was proposed for the synthesis of quinolines. Aromatic nitro compounds and ethanol/water solution were used as the starting materials, and Pt-Sn/γ-Al₂O₃was the catalyst. The quinolines were synthesized by the one-pot method with an in-situ liquid phase hydrogenation system. The reaction results showed that the Pt/Sn molar ratio and the reaction conditions including temperature and the concentration of the substrate and water played an important role on the yield of the quinolines. When the Pt/Sn molar ratio was 0.5, under the conditions of 220 ^oC, 5.0 MPa, 6% substituted nitrobenzene concentration with 70% EtOH and 30% H₂O solution, the total yield of 6-methoxyl-2-methyl quinoline reached 72.0%.

Key words: platinum, tin, aluminium oxide, in situ liquid phase hydrogenation, aromatic nitro compound, quinoline

GU Hui-Zi, XU Xiang-Sheng, CHEN Ao-Ang, YAN Xin-Huan. In-Situ Liquid Phase Catalytic Hydrogenation for One-Pot Synthesis of Quinolines from Aromatic Nitro Compounds[J]. Chinese Journal of Catalysis, 2012, 33(8): 1423-1426.

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References

1 De S K, Gibbs R A. Tetrahedron Lett, 2005, 46: 1647
2 陈广明, 吴志兵, 胡德禹, 杨松, 包文艳. 精细化工中间体 (Chen G M, Wu Zh B, Hu D Y, Yang S, Bao W Y. Fine Chem Intermediates), 2011, 41(2): 1
3 Ryckebusch A, Garcin D, Lansiaux A, Goossens J F, Baldeyrou B, Houssin R, Bailly C, Henichart J P. J Med Chem, 2008, 51: 3617
4 Narender P, Srinivas U, Ravinder M, Ananda Rao B, Ramesh Ch, Harakishore K, Gangadasu B, Murthy U S N, Jayathirtha Rao V. Bioorg Med Chem, 2006, 14: 4600
5 Ganguly A, Banerjee K, Chakraborty P, Das S, Sarkar A, Hazra A, Banerjee M, Maity A, Chatterjee M, Mondal N B, Choudhuri S K. Biomed Pharmacother, 2011, 65: 387
6 顾建华, 王毅, 郭仁德. 医学综述 (Gu J H, Wang Y, Guo R D. Medical Recapitulate), 2012, 18(1): 53
7 Iida H, Yuasa Y, Kibayashi C. J Org Chem, 1979, 44: 3985
8 Misani F, Bogert M T. J Org Chem, 1945, 10: 347
9 Gladiali S, Chelucci G, Mudadu M S, Gastaut M A, Thum-mel R P. J Org Chem, 2001, 66: 400
10 吴利欢, 杨定乔. 有机化学 (Wu L H, Yang D Q. Chin J Org Chem), 2010, 30: 1180
11 Ivachtchenko A V, Kobak V V, Ilyn A P, Khvat A V, Kysil V M, Willianms C T, Kuzovkova J A, Kravchenko D V. J Comb Chem, 2005, 7: 227
12 Doebner O, Miller W v. Ber, 1881, 14: 2812
13 Cho C S, Oh B H, Shim S C. J Heterocycl Chem, 1999, 36: 1175
14 Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576
15 Arcadi A, Chiarini M, Di Giuseppe S, Marinelli F. Synlett, 2003: 203
16 Kavitha C S, Hosamani K M, Harisha R S. Can J Chem, 2010, 88: 443
17 杨建峰, 孙军庆, 李小年, 严新焕. 催化学报 (Yang J F, Sun J Q, Li X N, Yan X H. Chin J Catal), 2006, 27: 559
18 严新焕, 李小年, 罗雄军, 孙军庆, 徐振元 (Yan X H, Li X N, Luo X J, Sun J Q, Xu Zh Y). CN 1 660 774. 2005
19 严新焕, 李小年, 罗雄军, 孙军庆, 徐振元 (Yan X H, Li X N, Luo X J, Sun J Q, Xu Zh Y). CN 1 660 771. 2005
20 Cortright R D, Davda R R, Dumesic J A. Nature, 2002, 418: 964
21 Huber G W, Shabaker J W, Dumesic J A. Science, 2003, 300: 2075
22 Zhou L, Gu H Z , Yan X H. Catal Lett, 2009, 132: 16
23 李小年, 项益智. 中国科学 B 辑 (Li X N, Xiang Y Zh. Sci China (Ser B)), 2007, 37: 136
24 沈颖旎, 罗智伟, 严新焕. 催化学报 (Shen Y N, Luo Zh W, Yan X H. Chin J Catal), 2008, 29: 612
25 Rangel M C, Carvalho L S, Reyes P, Parera J M, Figoli N S. Catal Lett, 2000, 64: 171

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