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

Synthesizing method for o-nitrobenzaldehyde compound

A technology of o-nitrobenzaldehyde and compounds, which is applied in the field of synthesis of organic compounds, can solve the problems of long reaction steps, different reaction steps, difficult region-specific synthesis, etc., and achieves good selectivity, simple reaction steps, low-end good adaptability

Active Publication Date: 2013-12-25
徐州宏阳新材料科技股份有限公司
View PDF1 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, o-nitrobenzaldehyde compounds containing various substituents on the market are rare due to the limitation of the positioning rules of the benzene ring, which makes o-nitrobenzaldehyde compounds containing various substituents on the benzene ring more difficult. Regiospecific synthesis requires longer reaction steps to synthesize the corresponding o-nitrobenzaldehyde, and different substituents involve different reaction steps, so there is no general method for synthesis

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
  • Synthesizing method for o-nitrobenzaldehyde compound
  • Synthesizing method for o-nitrobenzaldehyde compound
  • Synthesizing method for o-nitrobenzaldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Using benzaldehyde as raw material to synthesize 2-nitrobenzaldehyde

[0046]

[0047] (1) Add 0.530g (5.0mmol) of benzaldehyde, 1.12g (13.4mmol) of methoxyamine hydrochloride, 1.804g (22mmol) of anhydrous sodium acetate, 15ml of ethanol, and 45ml of water into a 100ml flask. The mixture was heated to reflux reaction, followed by TLC detection, the reaction was completed after 3 hours, the resulting mixed solution was extracted with 3×45mL ethyl acetate, the organic phase was taken and dried, and the solvent was removed under reduced pressure to obtain a light yellow liquid benzaldehyde-O-methyl Oxime 0.641g (95% yield).

[0048] (2) Add 67.5 mg (0.5 mmol) of benzaldehyde O-methyloxime, 11 mg (0.05 mmol) of palladium diacetate, 154 mg (1.0 mmol) of silver nitrite, 270 mg (1.0 mmol) of potassium persulfate and 1,2-bis Ethyl chloride (5ml) was successively added to a 10ml sealed pressure vessel. The mixture was heated and reacted in an oil bath at 110°C, followed by TL...

Embodiment 2

[0052] Synthesis of 4-trifluoromethyl-2-nitrobenzaldehyde from 4-trifluoromethylbenzaldehyde

[0053]

[0054] (1) Add 0.870g (5.0mmol) of 4-trifluoromethylbenzaldehyde, 1.12g of methoxyamine hydrochloride, 1.804g of anhydrous sodium acetate, 15ml of ethanol, and 45ml of water into a 100ml flask. The mixture was heated to reflux reaction, followed by TLC detection, and the reaction was completed after 3 hours. The resulting mixed solution was extracted with 3 × 45mL ethyl acetate, the organic phase was taken and dried, and the solvent was removed under reduced pressure to obtain a light yellow liquid 4-trifluoromethylbenzene Formaldehyde-O-methyloxime 0.995g (98% yield).

[0055] (2) 101.5mg (0.5mmol) of 4-trifluoromethylbenzaldehyde-O-methyloxime, 11mg (0.05mmol) of palladium diacetate, 154mg (1.0mmol) of silver nitrite, 270mg (1.0mmol) of potassium persulfate ) and 1,2-dichloroethane (5ml) were sequentially added to a 10ml sealed pressure vessel. The mixture was heated ...

Embodiment 3

[0059] Synthesis of 5-bromo-2-nitrobenzaldehyde from 3-bromobenzaldehyde

[0060]

[0061] (1) Add 0.915g (5.0mmol) of 3-bromobenzaldehyde, 1.12g of methoxyamine hydrochloride, 1.804g of anhydrous sodium acetate, 15ml of ethanol, and 45ml of water into a 100ml flask. The mixture was heated to reflux reaction, followed by TLC detection, the reaction was completed after 3 hours, the resulting mixed solution was extracted with 3 × 45mL ethyl acetate, the organic phase was taken and dried, and the solvent was removed under reduced pressure to obtain a light yellow solid 3-bromobenzaldehyde-O - Methyloxime 0.994 g (98% yield).

[0062] (2) 101.5mg (0.5mmol) of 3-bromobenzaldehyde-O-methyloxime, 11mg (0.05mmol) of palladium diacetate, 154mg (1.0mmol) of silver nitrite, 270mg (1.0mmol) of potassium persulfate and 1 , 2-dichloroethane (5ml) was sequentially added to a 10ml sealed pressure vessel. The mixture was heated and reacted in an oil bath at 110°C, followed by TLC detectio...

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 provides a preparation method for an o-nitrobenzaldehyde compound. The method directly taking benzaldehyde compounds as starting raw materials comprises the following steps: firstly, converting a formyl group into an O-methyl oximido; secondly, taking divalent palladium salt as a catalyst, and realizing the carbon-hydrogen bond activation single nitration reaction on an o-position of an oximido under the condition that both an oxidant and a nitration agent exist; finally, removing the O-methyl oximido by using strong organic acid to obtain the o-nitrobenzaldehyde compound. The nitration method provided by the invention has the advantage of specificity in the o-position of a nitration position, the reaction process is safe and environment-friendly, the substrate is excellent in adaptability, and various substituents can realize o-position nitration; various benzaldehyde is directly taken as raw materials, so that the reaction steps are simple, and the synthesizing method is a novel route for synthesizing various o-nitrobenzaldehyde compounds containing substituents.

Description

technical field [0001] The invention relates to a method for synthesizing an organic compound, in particular to a method for preparing an o-nitrobenzaldehyde compound. Background technique [0002] O-nitrobenzaldehyde compounds are important pharmaceutical intermediates, which can be used to synthesize nitropyridine (Niafedin), nisoldipine, encaramide and other raw materials for the treatment of cardiovascular diseases, and are also important organic synthesis raw materials. It is widely used in chemical industry. At present, o-nitrobenzaldehyde is mainly obtained from o-nitrotoluene through oxidation, hydrolysis or bromination, hydrolysis and other steps. However, o-nitrotoluene is obtained from toluene through mixed acid nitration, and excess nitric acid and sulfuric acid are required in the process. Strong acids are used as reaction reagents and catalysts, and a large amount of heat is released during the reaction process, which is likely to cause production hazards. At ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/44C07C201/12
Inventor 刘运奎张巍徐振元
Owner 徐州宏阳新材料科技股份有限公司
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