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以8-羟基喹啉、取代苯胺、亚硝酸钠和硫酸氢钾为原料,室温下经固相反应法合成了系列5-取代-8-羟基喹啉偶氮类化合物。实验结果显示,反应产物收率高低顺序与苯胺取代基团吸电子能力大小顺序相同。实验还考察了亚硝酸钠的用量、取代苯胺与8-羟基喹啉的物料配比等对反应产物收率的影响。结果表明,当氨基(—NH2)、8-羟基喹啉及亚硝酸钠物质的量比为1∶1.2∶1.04,反应时间为20 min时,目标产物的收率可分别达到最高为77.3%、86.1%、69.6%和48.1%。产物结构用核磁共振氢谱、碳谱、红外光谱、紫外-可见光谱及熔点进行了表征。
A series of 5-substituted-8-hydroxyquinoline azo compounds were synthesized by solid-state reaction at room temperature from 8-hydroxyquinoline, substituted aniline, sodium nitrite and potassium hydrogen sulfate. The experimental results show that the order of the yield of the reaction products is the same as that of the aniline substituent. The experiment also investigated the amount of sodium nitrite, substituted aniline and 8-hydroxyquinoline material ratio of the reaction product yield. The results showed that when the molar ratio of amino group (-NH2), 8-hydroxyquinoline and sodium nitrite was 1: 1.2: 1.04 and the reaction time was 20 min, the yield of the target product reached the maximum of 77.3% 86.1%, 69.6% and 48.1%. The structure of the product was characterized by 1H-NMR, GC, IR, UV-Vis and melting point.