CN114907260A - 一种利用离子液体制备4-溴甲基喹啉酮的方法 - Google Patents

一种利用离子液体制备4-溴甲基喹啉酮的方法 Download PDF

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CN114907260A
CN114907260A CN202210594422.0A CN202210594422A CN114907260A CN 114907260 A CN114907260 A CN 114907260A CN 202210594422 A CN202210594422 A CN 202210594422A CN 114907260 A CN114907260 A CN 114907260A
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韩宇辉
郭辉
王作堯
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High and New Technology Research Center of Henan Academy of Sciences
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Abstract

本发明提出了一种利用离子液体制备4‑溴甲基喹啉酮的方法，以离子液体为催化剂和溶剂，以溴化乙酰乙酰苯胺为原料进行环化脱水反应，合成4‑溴甲基喹啉酮。本发明以热稳定性好、难挥发、可循环使用的离子液体为催化剂和溶剂制备4‑溴甲基喹啉酮，不使用任何有毒有害的催化剂，操作简便，后处理简单，反应条件温和，产率高，是一种合成4‑溴甲基喹啉酮的绿色新方法。

Description

一种利用离子液体制备4-溴甲基喹啉酮的方法
技术领域
本发明涉及4-溴甲基喹啉酮的制备技术领域，特别是指一种利用离子液体制备4-溴甲基喹啉酮的方法。
背景技术
4-溴甲基喹啉酮是一类重要的含氮杂环化合物，可以作为中间体应用于抗溃疡药瑞巴匹特、N-苯氧烷胺类心血管药物等的合成。由于4-溴甲基喹啉酮在药物化学领域的重要应用，其合成方法的研究一直是关注的热点。传统方法主要有以下三种：
(1)先制备溴化乙酰乙酰苯胺，然后在浓硫酸催化下发生环化反应生成4-溴甲基喹啉酮，该方法由于使用浓硫酸作为环化反应的催化剂，不仅会导致苯环磺化的副反应，而且后处理时会产生大量废水，给环境带来危害；
(2)先制备溴化乙酰乙酰苯胺，然后在PPA催化下环化生成4-溴甲基喹啉酮，该方法虽然克服了浓硫酸催化下发生副反应的不足，但是后处理时仍会产生大量废水，给环境带来危害；
(3)先将溴化乙酰乙酰苯胺加入到无水有机溶剂中，在高温下发生环化脱水反应，利用有机溶剂与水形成共沸物将水带离反应体系，再利用五氧化二磷的强吸水性对有机溶剂干燥，该方法反应条件较为苛刻、操作较为复杂。因此，急需对4-溴甲基喹啉酮的制备方法进行改进，满足工业生产需求。
发明内容
为了解决现有技术中存在的对环境不友好、操作复杂以及催化剂难以循环使用等问题，本发明提出一种利用离子液体制备4-溴甲基喹啉酮的方法，以溴化乙酰乙酰苯胺为原料，以热稳定性好、难挥发、可循环使用的离子液体为催化剂和溶剂制备4-溴甲基喹啉酮。
本发明的技术方案是这样实现的：一种利用离子液体制备4-溴甲基喹啉酮的方法，以离子液体为催化剂和溶剂，以溴化乙酰乙酰苯胺为原料进行环化脱水反应，合成4-溴甲基喹啉酮。
Figure BDA0003667191140000021
进一步地，离子液体由阳离子和阴离子形成，阳离子为咪唑类或内酰胺类或季胺类阳离子，阴离子为四氟化硼或六氟化磷或硫酸氢根或磷酸二氢根或对甲苯磺酸根阴离子。
进一步地，离子液体为[NMPH]H2PO4、[NMPH]HSO4、[NMPH]PTSA、[HMIM]H2PO4、[HMIM]HSO4、[BMIM]HSO4、[EMIM]HSO4、[Me3NH]HSO4、[Et3NH]HSO4、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH2]HSO4、[Et3NH]H2PO4、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH2]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[BMIM]BF4、[BMIM]PF6、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4和[Bu2NH2]H2PO4中的一种或多种。
进一步地，溴化乙酰乙酰苯胺与离子液体的摩尔比为5：1-1：6。
进一步地，环化脱水反应的条件为：反应温度为15℃～120℃，反应时间在1～24小时。
进一步地，环化脱水反应后冷却至室温，对溶液进行萃取获得有机层，将有机层旋转蒸发除去萃取剂，得到粗产品，将粗产品经柱层析分离得到4-溴甲基喹啉酮，萃取后的离子液体经水洗干燥后循环应用。
进一步地，采用乙酸乙酯进行萃取。
本发明的有益效果：
本发明以对水和空气十分稳定的离子液体为催化剂和溶剂，以溴化乙酰乙酰苯胺为原料合成4-溴甲基喹啉酮。与传统方法相比，该方法不使用有毒有害的强酸催化剂，后处理不产生大量废水，对环境又好；操作简便，催化剂还可以循环使用，是一种合成4-溴甲基喹啉酮的绿色新方法。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
在反应容器中投入0.1摩尔溴化乙酰乙酰苯胺和0.3摩尔[NMPH]HSO4离子液体，50℃搅拌反应12小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为75％；离子液体经水洗干燥后，用于下一次合成反应。
1H NMR(400MHz,DMSO):δ＝4.96(s,3H),6.79(s,1H),7.28-7.32(m,1H),7.39(d,J＝8,1H),7.56-7.60(m,1H),7.89(d,J＝8,1H).13C NMR(100MHz,DMSO):δ＝30.02,116.23,117.44,122.18,122.70,125.29,131.15,139.72,147.19,161.71.产品核磁数据与参考文献(广东化工，2014，41(6)，70)的结果一致，证明所得产物为4-溴甲基喹啉酮。
实施例2
在反应容器中投入0.3摩尔溴化乙酰乙酰苯胺和0.5摩尔[Me3NH]HSO4离子液体，80℃搅拌反应12小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为70％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例3
在反应容器中投入1.0摩尔溴化乙酰乙酰苯胺和1摩尔[Et3NH]HSO4离子液体，100℃搅拌反应6小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为80％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例4
在反应容器中投入0.5摩尔溴化乙酰乙酰苯胺和0.3摩尔[BMIM]HSO4离子液体，100℃搅拌反应10小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为90％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例5
在反应容器中投入0.5摩尔溴化乙酰乙酰苯胺和0.5摩尔[HMIM]HSO4离子液体，90℃搅拌反应8小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为70％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例6
在反应容器中投入0.8摩尔溴化乙酰乙酰苯胺和0.5摩尔[HMIM]H2PO4离子液体，80℃搅拌反应12小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为65％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例7
在反应容器中投入1.0摩尔溴化乙酰乙酰苯胺和1.0摩尔[EMIM]HSO4离子液体，100℃搅拌反应10小时。反应结束后冷却至室温，然后加入乙酸乙酯萃取，合并有机层，旋转蒸发除去萃取剂得粗产品，再经柱层析分离得到4-溴甲基喹啉酮，反应的产率为80％；离子液体经过水洗干燥后，用于下一次合成反应。
实施例8-25
类似于实施例1，分别用[BMIM]BF4、[BMIM]PF6、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH]HSO4、[Et3NH]H2PO4、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4、[Bu2NH2]H2PO4、[NMPH]HSO4、[NMPH]TSOH做催化剂，在同样条件下进行反应，反应结束后得到如下结果(表一)：
表一
Figure BDA0003667191140000041
Figure BDA0003667191140000051
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (7)

1.一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：以离子液体为催化剂和溶剂，以溴化乙酰乙酰苯胺为原料进行环化脱水反应，合成4-溴甲基喹啉酮。
2.根据权利要求1所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：离子液体由阳离子和阴离子形成，阳离子为咪唑类或内酰胺类或季胺类阳离子，阴离子为四氟化硼或六氟化磷或硫酸氢根或磷酸二氢根或对甲苯磺酸根阴离子。
3.根据权利要求1或2所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：离子液体为[NMPH]H2PO4、[NMPH]HSO4、[NMPH]PTSA、[HMIM]H2PO4、[HMIM]HSO4、[BMIM]HSO4、[EMIM]HSO4、[Me3NH]HSO4、[Et3NH]HSO4、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH2]HSO4、[Et3NH]H2PO4、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH2]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[BMIM]BF4、[BMIM]PF6、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4和[Bu2NH2]H2PO4中的一种或多种。
4.根据权利要求1所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：溴化乙酰乙酰苯胺与离子液体的摩尔比为5：1-1：6。
5.根据权利要求1所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：环化脱水反应的条件为：反应温度为15℃～120℃，反应时间在1～24小时。
6.根据权利要求1所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：环化脱水反应后冷却至室温，对溶液进行萃取获得有机层，将有机层旋转蒸发除去萃取剂，得到粗产品，将粗产品经柱层析分离得到4-溴甲基喹啉酮，萃取后的离子液体经水洗干燥后循环应用。
7.根据权利要求6所述的一种利用离子液体制备4-溴甲基喹啉酮的方法，其特征在于：采用乙酸乙酯进行萃取。
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