4种8-羟基喹啉-7-醛缩芳香酰肼Schiff碱的合成及表征  

Syhthesis and characterization of four Schiff bases from 8-hydroxyquinoline-7-carboxyaldehyde and aroylhydrazines

作　　者：雷瑞霞[1] 程剑[1] 贾妍妍[1] 刘彩芬[1] 刘永春[1] 

机构地区：[1]陇东学院化学化工学院,甘肃庆阳745000

出　　处：《宝鸡文理学院学报（自然科学版）》2010年第2期24-27,共4页Journal of Baoji University of Arts and Sciences(Natural Science Edition)

摘　　要：目的合成4种8-羟基喹啉-7-醛-芳香酰腙新试剂。方法取以Rei mer-Tiemann反应原理制备的8-羟基喹啉-7-醛0.519 g(3 mmol)溶于30 mL 95%CH3CH2OH,在70～80℃条件下分别与等摩尔量异烟肼、苯甲酰肼、对羟基苯甲酰肼和邻羟基苯甲酰肼的10 mL 95%的CH3CH2OH溶液加热回流反应8 h后出现沉淀,冷却到室温后过滤分离,以80%甲醇水溶液重结晶,真空干燥24 h。结果和结论元素分析、熔点、1H NMR、MS以及IR谱的数据结果表明合成得到了8-羟基喹啉-7-醛-异烟酰腙、8-羟基喹啉-7-醛-苯甲酰腙、8-羟基喹啉-7-醛-对羟基苯甲酰腙和8-羟基喹啉-7-醛-邻羟基苯甲酰腙,分别为黄色、淡黄色、淡橙红色和淡橙红色粉末样品,产率分别为72.3%、73.4%、83.8%和83.2%。Aim To synthesize four new agents of 8-hydroxyquinoline-7-earboxyaldehyde-aroyl- hydrazones. Methods Reflux a mixture of 30 mL of 95% ethanol aquoues solution of 0. 519 g （3 mmol） 8-hydroxyquinoline-7-carboxyaldehyde synthesized by Reimer-Tiemann reaction with 10 mL of 95 % ethanol aquoues solution of equal molar amount of isonicotinylhydrazine, benzoylhydrazine, p- hydroxybenzoylhydrazine and o-hydroxybenzoylhydrazine at 70-80 ℃ for 8 h, respectively. After the reaction temperature cools to room temperature, a precipitate is obtained and filtered. Then the precipitate is recrystallized from 80% methanol aqueous solution and dried in vacuum over 24 h. The examples are analyzed by 1↑H NMR, MS and IR spectra. Results/Conclusion The data of elemental analysis, melting point, 1↑H NMR, MS and IR spectra indicated that they were 8-hydroxyquinoline-7- carboxyaldehyde-（isonicotinyl） hydrazone, 8-hydroxyquinoline-7-carboxyaldehyde-（benzoyl） hydrazone, 8-hydroxyquinoline-7-carboxyaldehyde-（p-hydroxybenzoyl） hydrazone and 8-hydroxyquinoline-7- carboxyaldehyde-（o-hydroxybenzoyl） hydrazone, respectively, with the color of a yellow, a pale yellow, a salmon pink and a salmon pink powder, and the yield of 72.3%, 73.4%, 83.8% and 83.2%.

关 键 词：REIMER-TIEMANN反应 8-羟基喹啉-7-醛 8-羟基喹啉-7-醛-芳香酰腙 SCHIFF碱 

分 类 号：O625.63[理学—有机化学]