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研究了离子液体[bmim]Cl-AlCl3催化4-甲氧基苯胺与丙烯酰氯反应一锅法合成6-羟基-3,4-二氢-2(1H)-喹啉酮,并用IR、1HNMR和元素分析对其结构进行确证。在[bmim]Cl-AlCl3介质中,4-甲氧基苯胺与丙烯酰氯发生酰化反应生成N-(4-甲氧基苯基)丙烯酰胺。而后在[bmim]Cl-AlCl3和酰化反应产生的HCl协同作用下,经过分子内Friedel-Crafts烷基化和脱甲基化反应,以89.6%的产率得到6-羟基-3,4-二氢-2(1H)-喹啉酮。离子液体[bmim]Cl-AlCl3作为催化剂和反应介质可以回收利用,重复使用5次目标产物的产率无明显降低。
The one-pot synthesis of 6-hydroxy-3,4-dihydro-2 (1H) -quinolinone catalyzed by [bmim] Cl-AlCl3 and 4-methoxyaniline with acryloyl chloride was studied. Elemental analysis confirms its structure. In [bmim] Cl-AlCl3 medium, 4-methoxyaniline acylates with acryloyl chloride to form N- (4-methoxyphenyl) acrylamide. After the [bmim] Cl-AlCl3 and the HCl produced by the acylation reaction, intramolecular Friedel-Crafts alkylation and demethylation gave 6-hydroxy-3,4- Dihydro-2 (1H) -quinolinone. The ionic liquid [bmim] Cl-AlCl3 can be recycled as a catalyst and reaction medium, and the yield of the target product after repeated use for 5 times is not obviously reduced.