6-甲氧基靛红的合成工艺改进

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6-甲氧基靛红的合成工艺改进

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉

文章导航 > 药学实践与服务 > 2015 > 33(2): 127-130

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

引用本文:

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

Citation:

WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

6-甲氧基靛红的合成工艺改进

doi: 10.3969/j.issn.1006-0111.2015.02.009

王鸿玉¹,
宋云龙²,
章玲²,
曾强²,
朱驹²,
张辉^3,

1.
沈阳药科大学制药工程学院, 辽宁沈阳 110016;第二军医大学药学院药物化学教研室, 上海 200433
2.
第二军医大学药学院药物化学教研室, 上海 200433
3.
沈阳药科大学制药工程学院, 辽宁沈阳 110016

基金项目: 国家自然科学基金项目(81172928,21102174)

Improvement of synthesis method of 6-methoxyisatin

1.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
2.
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
3.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China

摘要: 目的探索6-甲氧基靛红的合成工艺改进方法。方法以3-甲氧基苯胺为起始原料,经Sandmeyer方法首先生成中间体1-肟基-N-(3-甲氧基苯基)乙酰胺,在甲磺酸催化下关环得到6-甲氧基靛红。结果在关环反应中,催化剂采用甲磺酸,替代文献中常用的浓硫酸,温度80℃,反应30 min,收率达81.24%。结论提出了一条操作简单、条件温和、收率高的6-甲氧基靛红的合成工艺,适合大量制备。
- 6-甲氧基靛红 /
- 合成工艺 /
- 甲磺酸
Abstract: Objective To improve the synthetic condition of 6-methoxyisatin. Methods The starting material 3-methoxyaniline was firstly converted into the intermediate 1-oximino-N- (3-methoxyphenyl) acetamide through Sandmeyer reaction, then 6-methoxyisatin was conducted with methanesulfonic acid as catalyst in the following ring closure reaction. Results In the second step of the cyclization reaction, methanesulfonic acid was used to replace the concentrated sulfuric acid which is widely used in literature. The temperature was 80℃, the reaction time was 30 min, and the yield was 81.24%. Conclusion This study provided a synthesis process of 6-methoxyisatin with simple operation, mild reaction condition and high yield, which is suitable for large scale preparation of the compound.
- 6-methoxyisatin /
- synthesis /
- methanesulfonic acid

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6-甲氧基靛红的合成工艺改进

doi: 10.3969/j.issn.1006-0111.2015.02.009

1. 沈阳药科大学制药工程学院, 辽宁沈阳 110016;第二军医大学药学院药物化学教研室, 上海 200433

2. 第二军医大学药学院药物化学教研室, 上海 200433

3. 沈阳药科大学制药工程学院, 辽宁沈阳 110016

基金项目: 国家自然科学基金项目(81172928,21102174)

收稿日期: 2014-02-24
修回日期: 2014-09-10

关键词:

6-甲氧基靛红 /

摘要: 目的探索6-甲氧基靛红的合成工艺改进方法。方法以3-甲氧基苯胺为起始原料,经Sandmeyer方法首先生成中间体1-肟基-N-(3-甲氧基苯基)乙酰胺,在甲磺酸催化下关环得到6-甲氧基靛红。结果在关环反应中,催化剂采用甲磺酸,替代文献中常用的浓硫酸,温度80℃,反应30 min,收率达81.24%。结论提出了一条操作简单、条件温和、收率高的6-甲氧基靛红的合成工艺,适合大量制备。

English Abstract

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

引用本文:

王鸿玉, 宋云龙, 章玲, 曾强, 朱驹, 张辉. 6-甲氧基靛红的合成工艺改进[J]. 药学实践与服务, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

Citation:

WANG Hongyu, SONG Yunlong, ZHANG Ling, ZENG Qiang, ZHU Ju, ZHANG Hui. Improvement of synthesis method of 6-methoxyisatin[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 127-130. doi: 10.3969/j.issn.1006-0111.2015.02.009

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