氯化锆催化芳胺和正丁醛合成喹啉衍生物

Synthesis of quinoline derivatives from arylamine and n-butylaldehyde catalyzed by zirconium chloride

以ZrCl4为催化剂,芳胺和醛为原料,采用"一锅法"合成了喹啉衍生物;考察了空气、催化剂用量、原料比例以及芳胺的取代基等因素对反应收率的影响;利用高分辨质谱和核磁共振谱(1 H NMR、13 C NMR)表征了产物的分子结构.结果表明,以苯胺和正丁醛为原料时,3-乙基-2-丙基喹啉的收率可达65%,同时生成27%的N-丁基苯胺;工艺经改进后,反应条件温和、操作简便、催化剂用量少、产物收率高.

Quinoline derivatives were synthesized via one-pot reaction of aromatic amine and aldehyde in the presence of ZrCl4 catalyst. The effects of atmosphere, catalyst dosage, raw material ratios, and substituent of aniline on the yield were investigated. The molecular structure of assynthesized products was analyzed by high resolution mass spectrometry and nuclear magnetic resonance spectroscopy （1H NMR and 13C NMR）. Results show that the catalyzed reaction of aniline and n-butylaldehyde affords 3-ethyl-2-propylquinoline in a yield of 65 % and byproduct N-butylaniline in a yield of 27%. Thanks to the modification of reaction process, the established new method for synthesizing quinoline derivatives has advantages of mild reaction condition, convenient operation, high catalytic efficiency, and high yield.