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Quinoline derivative, synthesis method of derivative and catalyst for synthesis

A synthesis method and technology of derivatives, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc., can solve the complex product purification process, low utilization rate of raw materials, treatment Cumbersome and other problems, to reduce the production of side reactions and impurities, shorten the reaction time, and achieve the effect of good biodegradability

Active Publication Date: 2017-01-18
东港智科产业园有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the disadvantages of using an acidic ionic liquid to catalyze the synthesis of quinoline derivatives in the prior art when the ionic liquid catalyst is used in a large amount, the treatment before recycling is cumbersome, the raw material utilization rate is low, and the product purification process is complicated. Insufficient, provide a kind of quinoline derivative, the synthetic method of this derivative and its synthetic catalyst

Method used

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  • Quinoline derivative, synthesis method of derivative and catalyst for synthesis
  • Quinoline derivative, synthesis method of derivative and catalyst for synthesis
  • Quinoline derivative, synthesis method of derivative and catalyst for synthesis

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preparation example Construction

[0045] The flow chart of the synthetic method of quinoline derivative of the present invention is as figure 1 As shown, the specific steps are:

[0046] (1) Weigh the reaction raw materials 2-chloro-3-quinolinecarbaldehyde and β-diketone according to the molar ratio of 1:1.

[0047] (2) The weighed 2-chloro-3-quinoline formaldehyde and β-diketone are respectively added to methanol aqueous solution, and after fully dissolving and mixing, continue to add the molar amount of 2-chloro-3-quinoline formaldehyde 6~12% acidic ionic liquid catalyst, carry out heating reflux reaction under magnetic stirring condition, obtain solid precipitate, the volumetric amount of above-mentioned methanol aqueous solution in milliliter is 2-chloro-3-quinoline formaldehyde in millimole The molar weight is 7-10 times, the volume ratio concentration of methanol contained in the methanol aqueous solution is 88-93%, and the reaction pressure of the reflux reaction is 1 atmospheric pressure, and the refl...

Embodiment 1

[0054] 1mmol of 2-chloro-3-quinolinecarbaldehyde, 1mmol of barbituric acid and 0.08mmol of acidic ionic liquid were respectively added to 9ml of 90% aqueous methanol in a 50ml single-necked flask with a stirring bar and a condenser. Heated to reflux for 12 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, left to stand for 2 hours, suction filtered, and the filter residue was washed with methanol and dried in vacuo to obtain 5-(2-chloroquinoline -3-yl)methylene-2,4,6-pyrimidinetrione, the yield is 94%, and the filtrate is directly added with 2-chloro-3-quinoline formaldehyde and barbituric acid for repeated use. The performance parameters of 5-(2-chloroquinolin-3-yl)methylene-2,4,6-pyrimidinetrione obtained in this example are as follows: m.p.>300°C; IR (KBr): 3447, 1721, 1539cm -1 ; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.58(s, 1H), 7.93~8.02(m, 3H), 8.14(s, 1H), 8.30(s, 1H).

Embodiment 2

[0056] 1mmol 2-chloro-3-quinoline formaldehyde, 1mmol 2-thiobarbituric acid and 0.09mmol acidic ionic liquid were added respectively to the 50ml single-necked bottle containing 9ml 90% methanol aqueous solution with stirring bar and condenser . Heated to reflux for 14 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, left to stand for 3 hours, suction filtered, and the filter residue was washed with methanol and dried in vacuo to obtain 5-(2-chloroquinoline -3-base) methylene-2-mercapto-4,6-pyrimidinedione, the yield is 92%, after directly adding 2-chloro-3-quinoline formaldehyde and 2-thiobarbituric acid in the filtrate for reuse.

[0057] The performance parameters of 5-(2-chloroquinolin-3-yl)methylene-2-mercapto-4,6-pyrimidinedione obtained in this example are as follows: m.p.>300°C; IR(KBr):3441,1719, 1544cm -1 ; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.26-7.32 (m, 1H), 7.36-7.41...

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Abstract

The invention discloses a quinoline derivative, a synthesis method of the derivative and a catalyst for synthesis, and belongs to the technical field of organic chemical synthesis. The molar ratio of 2-chloro-3-quinoline formaldehyde and beta-dione in synthesis reaction is 1:1, the molar amount of an acidic ionic liquid catalyst is 6-12% of the used 2-chloro-3-quinoline formaldehyde, the volume amount of a reaction solvent methanol aqueous solution in ml is 7-10 times of the molar amount of the 2-chloro-3-quinoline formaldehyde in mmol, the reflux reaction time is 7-15 min, cooling is performed to room temperature after the reaction is finished, suction filtration is performed, and the filter residues are washed with methanol and vacuum-dried to obtain the quinoline derivative. Compared with synthetic methods using other catalysts, the method has low use amount of the catalyst, reusability without treatment, high raw material utilization rate, simple and convenient operation of the whole synthesis process and the like, and is advantageous for large-scale industrial application.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a quinoline derivative, a synthesis method of the derivative and a catalyst for synthesis thereof. Background technique [0002] Quinoline derivatives are a very important class of nitrogen-heterocyclic compounds, widely used in the synthesis of medicines, dyes, pesticides, food and feed additives, antioxidants, corrosion inhibitors, photosensitive materials, solvents and extractants, etc., especially in In the pharmaceutical industry, most quinoline derivatives have biological activities and pharmacological effects such as antimalarial, antibacterial, and antitumor. Among them, many quinoline derivatives with pharmacological effects are extracted from natural products, but more are synthesized by chemical methods. Therefore, it is of great significance to study the synthesis of quinoline derivatives. So far, the synthesis methods of quinoline der...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D401/06C07D405/06C07D417/06
CPCB01J31/0285C07D401/06C07D405/06C07D417/06
Inventor 沈智培沈建忠
Owner 东港智科产业园有限公司
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