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A kind of quinoline derivative, preparation method of the derivative and magnetic acidic nano material catalyst for preparation thereof

A nanomaterial and derivative technology, applied in the field of magnetic acid nanomaterial catalyst, can solve the problems of complex product purification process, large loss, low utilization rate of raw materials, etc. The effect of shortened reaction time

Active Publication Date: 2019-09-10
东港智科产业园有限公司
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Problems solved by technology

[0007] The purpose of the present invention is to overcome the ionic liquid catalyst that usually has a large loss in the process of recycling when using acidic ionic liquid to catalyze the preparation of quinoline derivatives in the prior art, and the catalyst needs to be dried before recycling, and the utilization rate of raw materials is low. Insufficiency of shortcomings such as complex product purification process, a quinoline derivative, a preparation method of the derivative and a magnetic acidic nanomaterial catalyst for its preparation are provided

Method used

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  • A kind of quinoline derivative, preparation method of the derivative and magnetic acidic nano material catalyst for preparation thereof
  • A kind of quinoline derivative, preparation method of the derivative and magnetic acidic nano material catalyst for preparation thereof
  • A kind of quinoline derivative, preparation method of the derivative and magnetic acidic nano material catalyst for preparation thereof

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preparation example Construction

[0037]A method for preparing quinoline derivatives of the present invention, the method uses 2-chloro-3-quinoline formaldehyde and β-diketone as reaction raw materials, and prepares quinoline derivatives under the catalytic action of a magnetic acid nanomaterial catalyst , the reaction equation is as follows:

[0038]

[0039] In the above formula, substance I is 2-chloro-3-quinoline formaldehyde, substance II is β-diketone, and substance III is the quinoline derivative prepared in the present invention, wherein the β-diketone is selected from In any one, the preparation method of the magnetic acidic nanomaterial catalyst used in the present invention, refer to related literature (Magnetic, acidic, ionic liquid-catalyzed one-pot synthesis of spirooxindoles [J], ACS Combinatorial Science, 2013, 15: 512~518 ), its structural formula is:

[0040]

[0041] The technological process of above-mentioned preparation method is as figure 1 As shown, the specific steps are:

...

Embodiment 1

[0050] 10mmol of 2-chloro-3-quinoline formaldehyde, 11mmol of barbituric acid and 2.14g of magnetic acidic nanomaterials were respectively added to 70ml of ethanol in a 250ml single-necked round bottom flask with a stirring bar and a condenser. Heat to reflux for 19 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, the catalyst is adsorbed with a magnet while it is hot, the remaining reaction solution is cooled to room temperature, the precipitated solid is crushed, left standing for 2 hours, suction filtered, the filter residue is washed with ethanol, After vacuum drying, 5-(2-chloroquinolin-3-yl)methylene-2,4,6-pyrimidinetrione was obtained with a yield of 91%, and the adsorbed catalyst was put into the filtrate to reconstitute the catalytic system. Direct addition of 2-chloro-3-quinoline carboxaldehyde and barbituric acid for repeated use.

[0051] The performance parameters of the present invention's gained 5-(2-chloroquinoline-3-yl)met...

Embodiment 2

[0053] Add 10mmol of 2-chloro-3-quinoline formaldehyde, 10mmol of 2-thiobarbituric acid and 1.98g of magnetic acidic nanomaterials into a 250ml single-necked round-bottomed flask containing 70ml of ethanol with a stirring bar and a condenser . Heated to reflux for 21 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, the catalyst was adsorbed by a magnet while it was hot, the remaining reaction solution was cooled to room temperature, the precipitated solid was crushed, left standing for 3 hours, suction filtered, the filter residue was washed with ethanol, After vacuum drying, 5-(2-chloroquinolin-3-yl)methylene-2-mercapto-4,6-pyrimidinedione was obtained with a yield of 90%, and the adsorbed catalyst was put into the filtrate to recombine the catalytic System, directly add 2-chloro-3-quinoline formaldehyde and 2-thiobarbituric acid for repeated use.

[0054] The performance parameters of the present invention's gained 5-(2-chloroquinolin-...

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Abstract

The invention discloses a quinoline derivative, a preparation method of the derivative and a magnetic acidic nanomaterial catalyst for its preparation, and belongs to the technical field of organic chemical synthesis. In the preparation reaction of the present invention, the molar ratio of 2-chloro-3-quinoline formaldehyde and β-diketone is 1:1 to 1.2, and the molar amount of the magnetic acidic nanomaterial catalyst is 10 of the 2-chloro-3-quinoline formaldehyde used. ~14%, the volume of the reaction solvent ethanol in milliliters is 5 to 7 times the molar amount of 2-chloro-3-quinolinecarbaldehyde in millimoles, the reflux reaction time is 10 to 24 minutes, and it is hot after the reaction is completed The catalyst is adsorbed with a magnet, and the remaining reaction solution is cooled to room temperature and filtered with suction. The filter residue is washed with ethanol and dried under vacuum to obtain the quinoline derivative. Compared with the preparation methods using other catalysts, the present invention has the characteristics of less catalyst loss, reusability without treatment, high raw material utilization rate, simple and convenient operation of the entire preparation process, etc., and is convenient for large-scale industrial application.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and more specifically relates to a quinoline derivative, a preparation method of the derivative and a magnetic acidic nano material catalyst for preparation thereof. Background technique [0002] Quinoline derivatives are a very important class of nitrogen-containing heterocyclic compounds. The main skeleton quinoline widely exists in bone oil and coal tar. It has very important applications in the fields of medicine, pesticides, dyes and chemical additives. With the wide application of such compounds in various fields, the research on their preparation routes and new catalyst systems has become more and more active. So far, the preparation methods of quinoline derivatives that have been developed mainly include Skraup method, Knoevenagel method, Doebner-Vonmiller method, Cambes method, Conrad-Limpach method, Friedlander method and "one-pot cooking" method. [0003] Ionic liqu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07D215/18C07D401/06C07D405/06C07D417/06
CPCC07D215/18C07D401/06C07D405/06C07D417/06B01J31/0292B01J31/0295B01J2231/342B01J35/40B01J35/33
Inventor 沈智培沈建忠卢华
Owner 东港智科产业园有限公司
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