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

Method for reducing aromatic nitro to arylamine

A technology for aryl nitro and aryl amine, applied in the field of reducing aryl nitro to aryl amine, can solve problems such as poor selectivity, and achieve the effects of low cost, high yield and high selectivity

Active Publication Date: 2017-06-06
宜昌尚诺德生物医药科技有限公司
View PDF8 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods still have disadvantages: when H2 is used as the reducing agent, special high-pressure equipment and flammable gas are required, and there is a certain risk; when hydrazine hydrate is used as the reducing agent , if the compound contains carbon-carbon double bonds, carbon-carbon triple bonds, or aldehyde groups, the selectivity is poor

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 reducing aromatic nitro to arylamine
  • Method for reducing aromatic nitro to arylamine
  • Method for reducing aromatic nitro to arylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Synthesis of aniline

[0063]

[0064] Nitrobenzene (0.6mmol, 74.0mg), water (6mmol, 108.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), toluene (1mL), under nitrogen protection , reacted at 50°C for 24h, TLC monitored the reaction, added 10mL of water, extracted with ethyl acetate (10mL×3), combined the organic phases, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by column chromatography (V petroleum ether: V acetic acid Ethyl ester=3:1), 34.6 mg of colorless liquid was obtained, namely, the target compound was obtained, and the yield was 62%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18

Embodiment 2

[0066] Synthesis of aniline

[0067]

[0068] Nitrobenzene (0.6mmol, 74.0mg), water (6mmol, 108.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), tetrahydrofuran (1mL), under nitrogen protection , reacted at 50°C for 24h, TLC monitored the reaction, added 10mL of water, extracted with ethyl acetate (10mL×3), combined the organic phases, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by column chromatography (V petroleum ether: V acetic acid Ethyl ester=3:1), 32.4 mg of colorless liquid was obtained, namely, the target compound was obtained with a yield of 58%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18

Embodiment 3

[0070] Synthesis of aniline

[0071]

[0072] Nitrobenzene (0.6mmol, 74.0mg), Pd / C (0.03mmol, 6.4mg) and tetrahydroxydiboron (1.5mmol, 134.5mg), methanol (1mL), reacted at 50°C for 24h under nitrogen protection, monitored by TLC To react, add 10 mL of water, extract with ethyl acetate (10 mL×3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V petroleum ether:V ethyl acetate=3:1), 33.0 mg of a colorless liquid was obtained, that is, the target compound was obtained with a yield of 59%. 1 H NMR (400MHz, CDCl 3 )δ:7.27-7.23(m,2H),6.86-6.83(m,1H),6.76(dd,J 1 =1.2Hz,J 2 =7.6Hz,2H),3.66(s,br,2H); 13 C NMR (100MHz, CDCl 3 )δ: 146.50, 129.38, 118.60, 115.18

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 relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for reducing an aromatic nitro group to an aromatic amine. Background technique [0002] Aromatic amines are also important organic synthesis intermediates and raw materials, which can be used to synthesize pesticides, medicines, rubber additives, dyes and pigments, synthetic resins, textile additives, surfactants, photosensitive materials and other fine chemicals. In addition, aromatic amines are common structural units in many bioactive drugs. Such as ADHD drug Adderall XR, anti-enteritis drug mesalamine, post-traumatic neuralgia drug Lyrica and other drugs. [0003] Regarding the preparation of aromatic amine compounds, the main methods reported at present can be obtained by reducing the corresponding aromatic nitro compounds. The methods for reducing aromatic nitro compounds in industry mainly include metal (iron powder, zinc powder, etc.) redu...

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): C07B43/04C07C209/36C07C211/46C07C211/47C07C211/51C07C211/52C07C213/02C07C217/84C07C221/00C07C225/22C07C253/30C07C255/58C07C231/12C07C233/43C07C237/30C07C237/40C07C227/06C07C229/56C07D213/73C07D215/38C07D215/40
CPCC07C213/02C07C221/00C07C231/12C07C253/30C07D213/73C07D215/38C07D215/40C07C227/04C07D217/22C07B43/04C07C209/325C07C217/84C07C225/22C07C255/58C07C233/43C07C237/30C07C229/56C07C211/46C07C211/47C07C211/51C07C211/52C07C237/40Y02P20/584
Inventor 周海峰周艳梅皮单违刘祈星刘森生
Owner 宜昌尚诺德生物医药科技有限公司
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