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Preparation method of 2-hydroxyl-3-butene-1-amine

A technology of butene and hydroxyl, applied in the field of preparation of 2-hydroxy-3-butene-1-amine, can solve the problems of cumbersome route, long time-consuming, large workload and the like, and achieves simple operation, short time-consuming and cost-effective low effect

Inactive Publication Date: 2016-04-20
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In the synthesis process of routes 2, 3 and 4, the process of removing the TMS protecting group is required. Such a route is cumbersome, requires a large amount of work, and takes a long time

Method used

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  • Preparation method of 2-hydroxyl-3-butene-1-amine

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Embodiment 1

[0045] A preparation method of 2-hydroxyl-3-butene-1-amine, specifically comprising the following steps:

[0046] (1) Add acrolein (1.12g, 0.02mol), trimethylsilyl cyanide (2.98g, 0.03mol) and lithium perchlorate trihydrate (3.21g, 0.02mol) successively to the reactor, and control the stirring speed to React at room temperature at 500r / min. During the reaction, the starting material acrolein used in the reaction was monitored by TLC. After the complete disappearance of the starting material, ethyl acetate was added, and the solid was removed by filtration. The obtained organic phase was washed three times with saturated brine, anhydrous Na 2 SO 4 After drying, 2-hydroxy-3-butene-1-carbonitrile was obtained by rotary evaporation.

[0047] In the above-mentioned TLC monitoring reaction process, the developing agent used is petroleum ether: ether=7:1;

[0048] The acrolein used in the above reaction: trimethylsilyl cyanide: lithium perchlorate trihydrate is 1mol: 1.5mol: 1mol; ...

Embodiment 2

[0062] A preparation method of 2-hydroxyl-3-butene-1-amine, specifically comprising the following steps:

[0063] (1) Add acrolein (1.12g, 0.02mol), trimethylsilyl cyanide (2.98g, 0.03mol) and lithium perchlorate trihydrate (6.42g, 0.04mol) successively to the reactor, and control the stirring speed to React at room temperature at 700r / min. During the reaction, the starting material acrolein used in the reaction was monitored by TLC. After the complete disappearance of the starting material, ethyl acetate was added, and the solid was removed by filtration. The obtained organic phase was washed three times with saturated brine, anhydrous Na 2 SO 4 After drying, 2-hydroxy-3-butene-1-carbonitrile was obtained by rotary evaporation.

[0064] In the above-mentioned TLC monitoring reaction process, the developing agent used is petroleum ether: ether=7:1;

[0065] The acrolein used in the above reaction: trimethylsilyl cyanide: lithium perchlorate trihydrate is 1mol: 1.5mol: 2mol; ...

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Abstract

The invention discloses a preparation method of 2-hydroxyl-3-butene-1-amine. The preparation method comprises the following specific steps: (1) taking acrolein as a start raw material to react with trimethylsilyl cyanide at room temperature in the presence of lithium perchlorate trihydrate to obtain 2-hydroxyl-3-butene-1-nitrile; (2) with diethyl ether or tetrahydrofuran as a solvent, reducing the 2-hydroxyl-3-butene-1-nitrile with lithium aluminum hydride to obtain a crude product of 2-hydroxyl-3-butene-1-amine; (3) making the crude product of 2-hydroxyl-3-butene-1-amine react with hydrochloric acid to obtain 2-hydroxyl-3-butene-1-amine hydrochloride; and (4) making the 2-hydroxyl-3-butene-1-amine hydrochloride react with alkali to finally obtain the 2-hydroxyl-3-butene-1-amine. According to the method disclosed by the invention, without a trimethylsilyl protection group removal process, the operation of reduced pressure distillation is avoided, the reaction path is shortened, and the operation is simple.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, and more specifically, relates to a preparation method of 2-hydroxy-3-buten-1-amine. Background technique [0002] 2-Hydroxy-3-buten-1-amine is an important chemical intermediate that is widely used in fields such as medicine and pesticides, and its structural formula is shown in formula (1). [0003] [0004] There are currently four methods for its chemical synthesis. [0005] Route one (J.Am.Chem.Soc.1950,72,4792), its reaction equation is as shown in formula (2): [0006] [0007] It adopts 3,4-epoxy-1-butene and ammonia water as raw materials, but the regioselectivity of ammonolysis of this synthesis route is low, and the target product 2-hydroxyl-3-butene-1-amine and by-product The product 2-amino-3-buten-1-ol is difficult to separate, which causes post-processing inconvenience, and the reaction yield is also low. [0008] Route 2 (J.Heterocycl.Chem.1990,27,811-812), in 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C213/08C07C215/24C07C253/00C07C255/15
CPCC07C213/02C07C213/08C07C253/00C07C215/24C07C255/15
Inventor 殷燕陶瑞衡朱耀华程凤凯孟凡丽段永斌潘金鹏孙玉星
Owner SHANGHAI INST OF TECH
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