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论文摘要 吡啶类化合物是有机合成中重要的原料与中间体，在医药和农药以及高分子材料等行业中具有广泛的应用，随着我国化学工业的飞速发展，对于吡啶类化合物的需求不断的增加，但是我国的吡啶合成水平与一些发达国家还是有一些差距，因此研究吡啶类化合物的合成是十分有意义的。本文研究了6-（N-Boc-氨甲基）-2-吡啶甲酸的合成路线。通过以下过程可以成功合成6-（N-Boc-氨甲基）-2-吡啶甲酸。23697
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首先用2,6-二甲基吡啶作为原料，通过加入高锰酸钾把6位上的甲基氧化为羧基，M2,6-二甲基吡啶。向化合物甲醇溶液中滴加SOCl2，再加NBS和AIBN回流反应，加水用乙酸乙酯萃取向含有产物的DMF溶液中加入邻苯二甲酰亚胺钾盐，室温反应，加入水合肼回流过夜。DIPEA和Boc2O，室温反应过夜，加入氢氧化锂得产物6-（N-Boc-氨甲基）-2-吡啶甲酸收率为78％。此合成路线具有周期短，原料廉价易得，工艺操作简便，反应条件温和，具有较高的工业应用价值。
毕业论文关键词：吡啶；6-（N-Boc-氨甲基）-2-吡啶甲酸；有机合成；Boc保护基团
Abstract
As the important raw materials and intermediates in organic synthesis, pyridine derivatives have been widely used in pesticide, medicine, polymer material industry. With the rapid development of chemical industry in our country, the pyridine compounds demand increases unceasingly, but our country pyridine synthesis level there are some gaps with developed countries still, synthesis so the research of Pyridines compounds is of great significance. This paper studied the synthesis route of 6-(N-Boc-aminomethyl)-2-picolinic acid. Through the following process can be successfully synthesized 6- (N-Boc- aminomethyl ) -2- picolinic acid.
The first 2,6- two methyl pyridine as raw material, by adding the 6 Potassium Permanganate methyl oxidation on the carboxyl group,M2,6- two methyl pyridine: To the compounds in methanol solution dropping SOCl2 refluxing, then add water, extracted with ethyl acetate, saturated sodium bicarbonate washing, drying with anhydrous sodium sulfate and concentrated in the protection of Ar gas plus NBS and AIBN refluxing, add water, ethyl acetate extraction, drying with anhydrous sodium sulfate, concentration, column chromatography, Potassium was added to phthalimide DMF solution containing products, adding hydrazine reflux overnight. Adding DIPEA and Boc2O , reaction at room temperature overnight, adding lithium hydroxide react , vacuum concentration, adding water, extracted with ethyl acetate, anhydrous Na2SO4, concentrated, column chromatography to obtain the product 6- (N-Boc- aminomethyl) -2- picolinic acid yield was 78%. This synthetic route cycle short, cheap and easily obtained raw materials, simple operation, mild reaction conditions, high industrial application value.
Keywords: pyridine; 6- (N-Boc- aminomethyl ) -2- pyridine carboxylic acid; organic synthesis; Boc group
目 录
1 前言 1
1.1吡啶的概述 1
1.2 吡啶类化合物的性质 2
1.3 吡啶类化合物的应用 2
1.3.1用于合成农药 2
1.3.2用于有机染料和化学发光试剂 3
1.3.3用于医药 3
1.4重要吡啶化合物的合成和生产方法 4
2 文献综述与方案论证 6
2.1文献综述 6
2.1.1相关的技术与知识介绍 6
2.1.2合成方法 9
2.3 确定实验路线 11
3 实验部分 13
3.1 试剂及仪器 13
3.1.1 试剂 13
3.1.2 仪器 15
3.2实验方法 16
3.2.1 2,6-2甲基吡啶甲酸的合成 16