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Method for synthesizing m-hydroxyphenylacetamide

A technology for m-hydroxyphenethylamine and hydroxyphenethylamine, which is applied in the field of synthesis of hydroxyarylethylamine, can solve problems such as numerous reaction steps and greater environmental harm, and achieves fewer experimental steps, higher yield and lower cost. Effect

Inactive Publication Date: 2009-01-07
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] Although the yield of each step of the method is high and the operation is simple and convenient, due to the various reaction steps, more corrosive raw materials such as thionyl chloride, ammonia water, concentrated hydrochloric acid and the like are used in the reaction, which is harmful to the environment.

Method used

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  • Method for synthesizing m-hydroxyphenylacetamide
  • Method for synthesizing m-hydroxyphenylacetamide
  • Method for synthesizing m-hydroxyphenylacetamide

Examples

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preparation example Construction

[0030] combine figure 1 , the synthetic method of m-hydroxyphenylethylamine of the present invention is to take m-hydroxybenzaldehyde as raw material to prepare m-hydroxyphenylethylamine through condensation, catalytic hydrogenation reduction, and its steps are as follows:

[0031] The first step, add solvent in m-hydroxybenzaldehyde and nitromethane, catalyst, carry out condensation reaction in reactor or reaction bottle; Wherein the solvent that adds is organic solvent, as ethyl acetate, dichloromethane, chloroform , tetrachloromethane, ether or petroleum ether. The mass ratio of m-hydroxybenzaldehyde to nitromethane is 1:1.5-1:1.7, and the amount of catalyst used is 20%-40% of the mass fraction of m-hydroxybenzaldehyde. The catalyst is a weak acid and weak base compound, such as NH 4 HCO 3 , NH 2 CH 2 CH 2 Oh. The condensation reaction temperature is 60°C-90°C, and the reaction time is 2h-6h.

[0032] In the second step, the reaction solution in the first step is po...

Embodiment 1

[0037] Embodiment 1: the synthesis of m-hydroxy-β-nitrostyrene

[0038] In a 250mL four-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, add m-hydroxybenzaldehyde (0.02mol), nitromethane (0.03mol), acetic acid (17mL) and ammonium acetate (0.007mol), Heat and stir, raise the temperature to 80°C, and keep warm for reaction. After the reaction was completed, the reaction system was cooled to room temperature, poured into an appropriate amount of ice water, and a yellow precipitate was precipitated. At this time, it is not necessary to filter, but directly heat the system to 60-70 ° C, and slowly add ethanol dropwise under stirring until the precipitate is completely dissolved, then pour the solution into an appropriate amount of ice water, and bright yellow needles are rapidly precipitated. crystals and sink to the bottom. Stand still for about 5 minutes. After the bright yellow crystals are precipitated, pour off the upper layer solution and...

Embodiment 2

[0039] Embodiment 2: the synthesis of m-hydroxyphenylethylamine

[0040] Dissolve an appropriate amount of m-hydroxy-β-nitrostyrene (50g) in a certain amount of methanol, put it into the hydrogenation reactor, add 0.5g5%Pd / C, feed nitrogen, replace 5 times, and then Hydrogen gas was introduced under stirring to make the pressure 2.5Mpa, then the temperature was raised to 100°C, the reaction was carried out for 2 hours, and the temperature was maintained for 1 hour. After the reaction is completed, ventilate, press filter, add an appropriate amount of hydrochloric acid solution to the reacted solution to make it acidic, and use CH 2 Cl 2 Extract, separate the water phase, and then add an appropriate amount of Na to the water phase 2 CO 3 The solution is made alkaline, distilled under reduced pressure, and then extracted with hot ethyl acetate, and the ethyl acetate solution is distilled under reduced pressure again to obtain the product.

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Abstract

The invention discloses a method for synthesizing m-hydroxy phenylethylamine from m-hydroxy benzaldehyde by condensation and catalytic hydrogenation. The method comprises the following steps: adding a solvent in m-hydroxy benzaldehyde, nitromethane and a catalyst, and carrying out condensation reaction in a reaction kettle; pouring the reactive solution in the precious step to an ice-water mixture to separate out yellow precipitate, and recrystallizing to obtain m-hydroxy-beta-nitrostyrene; and subjecting m-hydroxy-beta-nitrostyrene in the previous step to catalytic hydrogenation in a high-pressure kettle to obtain m-hydroxy phenylethylamine. The product synthesized by the method can meet the market requirements, that is to say, the color, the purity and the ignition residue of the product can meet the market requirements. The method has high yield, less experiment steps and low cost, and the organic solvent used in the entire synthesis process is nontoxic and cost-effective and can be recycled to reduce the solvent loss in industrial production. Liquid-phase catalytic hydrogenation reaction is selected to achieve easier recovery and higher yield of the product.

Description

A technical field [0001] The invention belongs to the preparation technology of substituted arylethylamine, in particular to a synthesis method of hydroxyarylethylamine. Two background technology [0002] The molecular formula of m-hydroxyphenylethylamine is as follows: [0003] [0004] As an important fine organic chemical intermediate, m-hydroxyphenylethylamine has a wide range of industrial applications and a large demand, and is widely used in medicine, dyes and organic synthesis. At present, there is only the production process of phenylethylamine in China, and the research on substituted arylethylamine is still in its infancy in China. Among them, phenylethylamine substituted by hydroxyl and alkoxy groups is an important drug intermediate, and the research on hydroxyphenylethylamine Research has only a few reports on p-hydroxyphenethylamine. [0005] The synthetic overview of p-hydroxyphenylethylamine is as follows: [0006] (1) p-hydroxyacetophenone method [...

Claims

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Application Information

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IPC IPC(8): C07C215/52C07C213/02
Inventor 程广斌吕春绪孙海龙
Owner NANJING UNIV OF SCI & TECH
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