Preparation method for m-aminophenylacetylene

A technology of aminophenylacetylene and nitrophenylacetylene, which is applied in the field of preparation of m-aminophenylacetylene, can solve the problems of unsuitability for industrial production, difficult control of reaction conditions, high product cost, etc., achieve simple and efficient reaction process, reduce production cost, The effect of little environmental pollution

Inactive Publication Date: 2014-04-16
CHONGQING WORLD HAORUI PHARM CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are easy to get, and there are five steps of reaction, but the reaction conditions of the selective debromination process are difficult to control, a large amount of reaction by-products will be produced, and the yield is as low as 45%, resulting in higher product costs, so it is not suitable for industrial production

Method used

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  • Preparation method for m-aminophenylacetylene
  • Preparation method for m-aminophenylacetylene
  • Preparation method for m-aminophenylacetylene

Examples

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Embodiment 1

[0034]Preparation of dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent). Add 33.2g (0.2mol) of dimethyl acetonyl phosphate and 300ml toluene in sequence in a 1000ml reaction flask, add 5.1g (0.21mol) of NaH in batches, and after all the gas is released, p-toluenesulfonyl azide A mixture of 41.4g (0.21mol) and 500ml of tetrahydrofuran was added to the reaction solution and reacted at room temperature for 16h. After the reaction, dilute with petroleum ether, filter, wash the filter cake with diethyl ether, evaporate the solvent under reduced pressure to obtain 33.1 g of yellow liquid with a yield of 86.5%.

Embodiment 2

[0036] Preparation of dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent). Add 33.2 g (0.2 mol) of dimethyl acetonyl phosphate and 300 ml tetrahydrofuran in sequence in a 1000 ml reaction bottle, add 8 g (0.2 mol) of sodium hydride in batches, and after all the gas is released, p-toluenesulfonyl azide A mixture of 47.3g (0.24mol) and 500ml tetrahydrofuran was added to the reaction solution and reacted at room temperature for 12h. After the reaction, add petroleum ether to dilute, filter, wash the filter cake with ether, evaporate the solvent under reduced pressure, and obtain 33.7 g of yellow liquid with a yield of 88%.

Embodiment 3

[0038] Preparation of m-nitrophenylacetylene. Add 15.1 g (0.1 mol) of m-nitrobenzaldehyde and 18.3 g of homemade (1-diazo-2-oxopropyl)phosphonic acid dimethyl ester (Bestmann-Ohira reagent) in a dry and clean 1000 ml reaction bottle (0.11mol) (purified) and 750ml of methanol, cooled to 0-5°C, slowly added 20.7g (0.15mol) of anhydrous potassium carbonate, the temperature was controlled at 0-5°C during addition, after the addition, keep stirring for 2h. Then the reaction temperature was raised to room temperature, and the stirring reaction was continued for 8h. Stop the reaction, add saturated ammonium chloride aqueous solution, dichloromethane 150ml×3 extract, combine the organic phases, and dry over anhydrous sodium sulfate for 2h. Filter, wash the filter cake with an appropriate amount of dichloromethane, combine the organic phases, concentrate under reduced pressure to recover the solvent, freeze and solidify to obtain 13.1 g of a light yellow solid, with a yield of 89.2%. ...

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Abstract

The invention discloses a preparation method of m-aminophenylacetylene. The preparation method comprises the following steps: allowing dimethyl acetylmethylphosphonate to react with 4-methylbenzenesulfonylazide under a strong-alkali condition to obtain (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester; allowing the (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester to react with m-nitrobenzaldehyde under a catalytic condition to obtain 3-nitrophenylacetylene; finally, reducing the 3-nitrophenylacetylene to obtain the m-aminophenylacetylene. The preparation method has the advantages as follows: the starting raw materials are convenient and easy to obtain; the process route is simple and reasonable; the cost is low; three-waste pollution is small; large scale production is achieved; the product quality is good; the yield is high.

Description

technical field [0001] The invention relates to a preparation method of m-aminophenylacetylene, belonging to the fields of organic chemistry and medicinal chemistry. Background technique [0002] m-Aminophenylacetylene, also known as 3-ethynylaniline, has two functional groups, amino and alkynyl, and can derive a series of important intermediates. The structural formula is: [0003] [0004] m-aminophenylacetylene itself has good mechanical properties and high mechanical strength, can withstand quite high torsional shear force, and has very good high temperature resistance and wear resistance. It reacts with maleic anhydride to form polyimides The compound is extremely important. The resin made of this polymer has high thermal stability and high mechanical strength. It is a high-grade resin used in the synthesis of aviation, aerospace, military and other fields, and can be applied to the empennage of aircraft And the shell of the missile; m-aminophenylacetylene and quin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/45C07C209/36C07C205/06C07C201/12
Inventor 陈晓朋林松林国跃
Owner CHONGQING WORLD HAORUI PHARM CHEM
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