Oxidant Effect of H2O2 for the Syntheses of Quinoline Derivatives via One-Pot Reaction of Aniline and Aldehyde |
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| Authors: | Qiaoxia Guo Wennian Wang Weiling Teng Liwei Chen Yanqing Wang Baojian Shen |
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| Institution: | 1. State Key Laboratory of Heavy Oil Processing, College of Science, China University of Petroleum , Beijing , China qxguo@cup.edu.cn;3. State Key Laboratory of Heavy Oil Processing, College of Science, China University of Petroleum , Beijing , China |
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| Abstract: | A convenient one-pot method for the synthesis of substituted quinolines via the reaction of aniline and aldehyde in the presence of a Lewis acid (AlCl3) and an oxidant (H2O2) has been developed. Hydrogen peroxide was found to promote the reaction by its function as a hydrogen hunter, hindering the formation of by-product N-alkylaniline. The effect of the oxidant on the yield and selectivity was studied. When the molar ratio of aniline, n-butyraldehyde, and H2O2 was 1:3:0.5 at 25 °C, the yield of 3-ethyl-2-propylquinoline was improved from 64% (reaction without H2O2) to 84% (with H2O2), and the quinoline selectivity was improved to almost 100%. Moreover, the reaction time was obviously reduced. The substituent effect was also investigated in this work. |
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| Keywords: | Aldehyde aniline hydrogen peroxide oxidation quinoline derivatives |
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