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Method for synthesizing 2-hydro-2-substitued-quinoline derivative compound

A synthesis method and compound technology, which is applied in the field of synthesis of 2-hydrogen-2-substituted-quinoline derivatives, can solve the problems of complicated separation process, increased cost, and product deterioration, and achieve the effect of convenient use

Inactive Publication Date: 2012-10-03
CHANGZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional methods often require high temperature or strong acid environment, and will lead to product deterioration, resulting in complicated separation process
It has been reported that quinoline is synthesized by noble metal catalysis, but the cost of synthesis increases. With the proposal of "atom economy" and "green chemistry", transition metal catalyzed amino substitution of allyl alcohol has become a hot spot of scientific research in recent years.

Method used

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  • Method for synthesizing 2-hydro-2-substitued-quinoline derivative compound
  • Method for synthesizing 2-hydro-2-substitued-quinoline derivative compound
  • Method for synthesizing 2-hydro-2-substitued-quinoline derivative compound

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Experimental program
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Effect test

Embodiment 1

[0022] Synthesis of 2-hydrogen-2-substituted-quinoline derivatives compounds shown in embodiment 1, formula (II)

[0023]

[0024] In a dry reactor, add 0.05 mmol FeCl 3 With 0.5mmol allyl alcohol, vacuumize and change nitrogen three times, add 2ml toluene under nitrogen protection, stir and heat up to 110°C in oil bath for 12h reaction, until the first step is completely reacted, add 10eq of sodium hydroxide to keep the original temperature, reacted for 12 hours, cooled to room temperature, and the reaction solution was directly put on the column, and subjected to column chromatography (eluent: PE:EtOAC=10:1), the yield: 85%. Melting point: 81-83°C; 1 H NMR: δ8.16-8.23(m,4H),7.86-7.89(d,J=8.8,1H),7.81-7.83(d,J=8.4,1H),7.71-7.75(dd,J=6.8, 8.4,1H),7.51-7.55(m,3H),7.44-7.48(t,J=7.2,1H). 13 C NMR: δ119.0, 126.3, 127.2, 127.5, 127.6, 128.9, 129.3, 129.6, 129.7, 136.8, 139.7, 148.3, 157.4. IR (neat): 3058, 2960, 2926, 1597, 772.8. HRMS (EI): [ M] + calculated for C 15 h 1...

Embodiment 2

[0025] Synthesis of 2-hydrogen-2-substituted-quinoline derivative compounds shown in embodiment 2, formula (II)

[0026] In a dry reactor, add 0.025mmol Ag and 0.5mmol allyl alcohol, vacuumize and change nitrogen three times, add 2ml of toluene under nitrogen protection, stir and heat the oil bath to 110°C for 12h, wait for the first step to complete the reaction, directly Add 10eq of sodium hydroxide, keep the original temperature, react for 12h, cool to room temperature, the reaction solution is directly passed through the column, and the product is separated by column chromatography (eluent: PE:EtOAC=10:1), the yield is 90.2% .

Embodiment 3

[0027] Synthesis of 2-hydrogen-2-substituted-quinoline derivative compounds shown in embodiment 3, formula (II)

[0028] In a dry reactor, add 0.025 mmol FeCl 3 and 0.5mmol allyl alcohol, under air condition, add 2ml dichloromethane, stir at room temperature, until the first step reaction is complete, directly add 10eq sodium hydroxide, 0.1ml ethanol, heat to 60°C, react for 12h, cool to At room temperature, the reaction solution was directly passed through the column, and the product was separated by column chromatography (eluent: PE:EtOAC=10:1) with a yield of 95%.

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Abstract

The invention relates to a method for synthesizing a 2-hydro-2-substitued-quinoline derivative compound, which belongs to the technical field of synthesis of organic compounds. The method comprises the following steps of: adding allyl alcohol, a metal catalyst and a reaction solvent serving as raw materials into a reactor; stirring at the temperature of 0-220 DEG C for 0.5-36 hours; and extracting with an organic solvent, concentrating with a rotary evaporimeter, and passing through a column to obtain the 2-hydro-2-substitued-quinoline derivative compound. The method is easy and efficient; and a metal salt is taken as a catalyst, so that a reaction can be performed at a low temperature, and convenience is brought to use.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of 2-hydrogen-2-substituted-quinoline derivatives. Background technique [0002] Quinoline has anti-malarial, anti-asthma, anti-bacterial and anti-viral properties and is the backbone of many biologically active molecules. There are many known methods for our reference to synthesize this type of compound, the most typical one is the Skraup method, in which aniline, glycerin and concentrated sulfuric acid are heated in the presence of nitrobenzene as an oxidant, and a violent exothermic reaction is generated to generate quinoline. Traditional methods often require high temperature or strong acid environment, and will lead to product deterioration, resulting in complicated separation process. It has been reported that quinoline is synthesized by noble metal catalysis, but the cost of synthesis increases. With the proposal of "atom ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/04C07D215/12
Inventor 王治明王钰蓉吴海波李申李小明孙小强
Owner CHANGZHOU UNIV