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Preparation method of 2-methylquinoline

A technology of methylquinoline and nitrobenzene, which is applied in the field of preparation of 2-methylquinoline, can solve the problems of complex process, unfriendly environment, harsh reaction conditions, etc., and achieve less reaction equipment and simple and easy preparation method , the effect of less preparation steps

Active Publication Date: 2020-05-15
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And it usually needs to be in strong acid, high temperature and high pressure environment, the reaction conditions are harsh, the process is complicated, and it is not friendly to the environment

Method used

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  • Preparation method of 2-methylquinoline
  • Preparation method of 2-methylquinoline
  • Preparation method of 2-methylquinoline

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Experimental program
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Effect test

Embodiment 1

[0029] Accurately weigh 0.005mmol palladium acetate catalyst, add 10mL into the Young's reaction tube which has been placed in the magnetic stirrer, replace the oxygen in the Young's reaction tube three times, make the reaction proceed under the oxygen condition, and accurately add into the Young's reaction tube with a syringe 0.4mmol silver tetrafluoroborate, 0.1mmol pivalic acid, 0.2mmol nitrobenzene and 1ml ethanol, put the above-mentioned Young's reaction tube on a magnetic stirrer, and stir at 180°C for 24h; after the reaction, column the reaction solution The pure product of 2-methylquinoline was obtained by chromatography with a yield of 81%.

[0030] The above-mentioned obtained 2-methylquinoline has been characterized and tested:

[0031] as attached figure 1 Shown, the 2-methylquinoline prepared by this method 1 H-NMR, its compound characterization data: 1 H-NMR (400MHz, CDCl 3 ): δ (ppm) = 2.65 (s, 3.0H), 7.10 (d, J = 8.0Hz, 1.0H), 7.38 (m, 1.0H), 7.58 (m, 1.0H)...

Embodiment 2

[0035] Accurately weigh 0.005mmol of palladium acetate catalyst, add 10mL into the Young's reaction tube which has been placed in a magnetic stirrer, and accurately add 0.4mmol of silver tetrafluoroborate, 0.1mmol of pivalic acid, and 0.2mmol of nitrobenzene into the Young's reaction tube with a syringe and 1ml of ethanol, the above-mentioned Young's reaction tube was placed on a magnetic stirrer, and stirred at 100°C for 24h; after the reaction, the reaction solution was subjected to column chromatography to obtain the pure product of 2-methylquinoline, with a yield of 32%. .

Embodiment 3

[0037] Accurately weigh 0.01mmol of palladium acetate catalyst, add 10mL into the Young's reaction tube which has been placed in the magnetic stirrer, replace the oxygen in the Young's reaction tube three times, make the reaction proceed under the oxygen condition, and accurately add into the Young's reaction tube with a syringe 0.4mmol silver acetate, 0.2mmol trifluoroacetic acid, 0.2mmol nitrobenzene and 1ml ethanol, put the above-mentioned Young's reaction tube on a magnetic stirrer, stir at 140°C for 24h; after the reaction, perform column chromatography on the reaction solution The pure product of 2-methylquinoline was obtained with a yield of 68%.

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Abstract

The invention discloses a preparation method of 2-methylquinoline, wherein the preparation method comprises the following synthesis steps: in the presence of an oxidant, adding a catalyst and an adjuvant, and adding nitrobenzene and ethanol to perform one-step reaction to obtain a 2-methylquinoline target product, wherein the catalyst comprises a metal catalyst, an auxiliary agent I and an auxiliary agent II, the metal catalyst is a palladium metal catalyst, the auxiliary agent I is a silver-containing compound, and the auxiliary agent II is an acidic compound. Nitrobenzene and ethyl alcohol are used as raw materials, 2-methylquinoline can be prepared through one-step reaction of the method, and the preparation method is simple, convenient and easy to implement; the preparation process does not generate new three wastes, is environment-friendly, and provides a green and environment-friendly synthesis method for adapting to the development of the times; the preparation method has the advantages of fewer raw material types, fewer reaction equipment, fewer preparation steps and lower cost, and is more suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic intermediates, in particular to a preparation method of 2-methylquinoline. Background technique [0002] 2-Methylquinoline, also known as quinaldine, has a molecular formula of C10H9N, a colorless oily liquid. Soluble in ethanol, ether, acetone and chloroform, slightly soluble in water. 2-Methylquinoline is an important organic chemical intermediate, which is widely used in the production of alkalinizers for color film, photographic sensitizers, rubber vulcanization accelerators, antioxidants for lubricating oil, insecticides, and fungicides and dyes etc. [0003] At present, there are two main ways of industrial production of 2-methylquinoline compounds: coal tar extraction method and chemical synthesis method. [0004] Wherein the coal tar extraction method is to use coal tar or isoquinoline still slag (fraction) as raw material, through steps such as phosphate double salt method extraction, ...

Claims

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Application Information

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IPC IPC(8): C07D215/04
CPCC07D215/04
Inventor 李纪兴丛文霞
Owner LINYI UNIVERSITY
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