Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing arylamine by reducing aromatic nitro compound

An aromatic nitro compound technology is applied in the field of aromatic nitro compound reduction to prepare aromatic amine, and achieves the effects of good reaction selectivity, less waste liquid discharge and simple treatment

Inactive Publication Date: 2016-07-13
NANJING UNIV OF SCI & TECH
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is simple to operate, but requires the use of toxic and volatile organic solvents as the medium

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
  • Method for preparing arylamine by reducing aromatic nitro compound
  • Method for preparing arylamine by reducing aromatic nitro compound
  • Method for preparing arylamine by reducing aromatic nitro compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 1mmol of 3,4-dimethylnitrobenzene (151.2mg), 4-nitrobenzyl bromide (216.0mg), 4-nitrochlorobenzene (157.6mg), 2-chloro-5-nitroaniline (172.6 mg), 4-chloro-2-nitroaniline; one of (172.6 mg), 0.3 mmol NaOH (12.0 mg), 1% mmol Pd(OAc) 2 (2.3mg), ionic liquid (100mg), H 2 Add 1.5mL of O1.5mL to the pressure tube and stir evenly, add 5mmol hydrazine hydrate, react in 50°C oil bath for 20h, add 2mL ethyl acetate to extract three times after the reaction is stopped, remove the organic solvent by rotary evaporation, and pass through column chromatography on silica gel , to obtain pure target products 1a-1e, the yields are 90%, 98%, 97%, 96%, 99%, respectively, as shown below.

[0022]

Embodiment 2

[0024] Take 1mmol of p-nitroanisole (153.1mg), m-nitroaniline (138.1mg), o-fluoronitrobenzene (141.1mg), 4-fluoro-3-nitrotoluene (155.1mg) respectively , 0.3mmolKOH(16.9mg), 1%mmolPd(OAc) 2 (2.3mg), ionic liquid (100mg), H 2 Add 1.5mL of O1.5mL to the pressure tube and stir evenly, add 5mmol hydrazine hydrate, react in 50°C oil bath for 20h, add 2mL ethyl acetate to extract three times after the reaction is stopped, remove the organic solvent by rotary evaporation, and pass through column chromatography on silica gel , the pure target products 2a-2d were obtained, and the yields were 95%, 98%, 98%, and 85%, respectively, as shown below.

[0025]

Embodiment 3

[0027] Take 1mmol of 6-nitroquinoline (174.2mg), p-bromonitrobenzene (202.01mg), p-chloronitrobenzene (157.6mg), p-nitrophenol (139.1mg), m-nitrophenol (139.1mg) , one of o-nitrotoluene (137.1mg), 0.3mmolK 2 CO 3 (41.5mg), 1%mmolPd(OAc) 2 (2.3mg), ionic liquid (100mg), H 2 Add 1.5mL of O1.5mL to the pressure tube and stir evenly, add 5mmol hydrazine hydrate, react in 50°C oil bath for 20h, add 2mL ethyl acetate to extract three times after the reaction is stopped, remove the organic solvent by rotary evaporation, and pass through column chromatography on silica gel , the pure target products 3a-3f were obtained, and the yields were 94%, 90%, 99%, 78%, 97%, 83%, respectively, as shown below.

[0028]

[0029]

[0030] The inventors also synthesized the following ionic liquids:

[0031]

[0032] And they were applied to the reduction reaction of aromatic nitro compounds. It was found that the ionic liquid formed by connecting different groups of imidazole 3 had diff...

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 method for preparing arylamine by reducing an aromatic nitro compound.The method includes the steps that the aromatic nitro compound, palladium acetate, alkali and ion liquid are added into a reaction container, water is added to serve as solvent, the mixture is stirred to be uniform, finally hydrazine hydrate is added to serve as a reducing agent, and heating and stirring are conducted for a reaction; after the reaction is completed, an obtained product is extracted through organic solvent, the solvent is removed in a rotary evaporateion mode, and the product is obtained through column chromatography silica gel.The method has the advantages that the reaction is conducted in a water phase, the hydrazine hydrate serves as the reducing agent, organic solvent and a high-pressure device are omitted in the reaction process, and emission of toxic waste gas and waste liquid in the reaction process is lowered; reaction postprocessing is simple, less waste liquid is discharged, and a water phase catalysis system can be recycled and reused through simple liquid diversion; reaction selectivity is good, and the yield is high.

Description

technical field [0001] The invention relates to a method for preparing aromatic amines by reduction of aromatic nitro compounds, belonging to the field of organic synthesis. Background technique [0002] Aromatic amines are important organic synthesis intermediates and raw materials for the synthesis of pesticides, pharmaceuticals, rubber additives, dyes and pigments, synthetic resins, textile auxiliaries, surfactants, photosensitive materials and other fine chemicals. Only one representative product, aniline, has an annual output of about 1.6 million tons in the world, and the annual production capacity of aniline in my country is about 250,000 tons. With the development of my country's chemical industry, especially the rapid development of fine chemicals, its The scope of application is constantly expanding, and the market prospect is promising. The reduction of aromatic nitro compounds to corresponding aromatic amines is easy to operate and the raw materials are easy to o...

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): C07C209/36C07C211/46C07C211/52C07C211/51C07C213/02C07C217/84C07D215/38C07C215/76
CPCC07C209/36C07C213/02C07C215/76C07C211/46C07C211/52C07C211/51C07C217/84
Inventor 陆国平许祝兵张龙梦姝
Owner NANJING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com