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
View PDF4 Cites 0 Cited by
  • 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 re

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 2-methylquinoline
  • Preparation method of 2-methylquinoline
  • Preparation method of 2-methylquinoline

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0028] Example 1

[0029] Accurately weigh out 0.005mmol of palladium acetate catalyst, add 10mL into the Young's reaction tube that has been placed in the magnetic stirrer, and perform oxygen replacement in the Young's reaction tube three times to make the reaction proceed under oxygen conditions, and use a syringe to accurately add to the Young's reaction tube 0.4mmol silver tetrafluoroborate, 0.1mmol pivalic acid, 0.2mmol nitrobenzene and 1ml ethanol, put the above Young’s reaction tube on a magnetic stirrer, stir at 180℃ for 24h; after the reaction, the reaction solution is columned The pure product of 2-methylquinoline was obtained by chromatography, and the yield was 81%.

[0030] The 2-methylquinoline obtained above was characterized and tested:

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

Example Embodiment

[0034] Example 2

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

Example Embodiment

[0036] Example 3

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D215/04
CPCC07D215/04
Inventor 李纪兴丛文霞
Owner LINYI UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap