Pyridine-2''amino-2'-hydroxybenzene methanol phenylcarbinol boric acid ester compound and synthetic method thereof

A technology of hydroxybenzyl alcohol and borate esters, which is applied in the field of pyridine-2”-amino-2’-hydroxybenzyl alcohol borate ester compounds and their synthesis, which can solve environmental hazards, high toxicity and release of by-products hydrocyanic acid, The problem of low yield is achieved, and the effect of simple synthesis and abundant raw materials is achieved

Inactive Publication Date: 2009-08-26
LIAONING UNIVERSITY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]First, the reductive amination of Pd, Ni, Pt and other metal catalytic hydrogenation is a heterogeneous reaction, usually carried out under pressure, and the method is economical and simple , has been used in the industrial preparation of several amines, but the disadvantage is that most of the obtained mixtures are generally obtained, and the yield is not high
But they all have their own disadvantages, and all of them are very harmful to the environment.
Because the former is highly toxic and there is a danger of releasing by-product hydrocyanic acid; the latter needs to use a large amount of corrosive acetic acid in the preparation process

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
  • Pyridine-2''amino-2'-hydroxybenzene methanol phenylcarbinol boric acid ester compound and synthetic method thereof
  • Pyridine-2''amino-2'-hydroxybenzene methanol phenylcarbinol boric acid ester compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthesis of pyridine-2 "-amino-2'-hydroxybenzyl alcohol borate

[0020] Accurately weigh 0.50g (4.1mmol) of salicylaldehyde and dissolve it in 10mL of ethanol, simultaneously weigh 0.39g (4.1mmol) of 2-aminopyridine and dissolve it in 10mL of ethanol, and add the latter dropwise to the ethanol solution of salicylaldehyde , After heating and refluxing under stirring for 5 hours, the ethanol was evaporated under reduced pressure, and recrystallized with 10 mL of ethanol to obtain the product salicylaldehyde acetal 2-aminopyridinium, with a yield of 84.5%.

[0021] Accurately weigh 2.40 g (12.1 mmol) of salicylaldehyde acetal 2-aminopyridinzanthine and dissolve in 20 mL of ethanol-water (V:V=4:1), and then add 0.75 g (12.1 mmol) of boric acid. Control the reflux temperature to 75-80° C., react for 2 hours, filter the obtained solution, extract and place it, and the product is precipitated with a yield of 58.3%.

[0022] verify: 1 H NMR (CD 3 OD) δ6.56...

Embodiment 2

[0024] Example 2: Synthesis of pyridine-2"-amino-3', 5'-dimethyl-2'-hydroxybenzyl borate

[0025] Accurately weigh 0.61g (4.1mmol) of 3,5-dimethyl salicylaldehyde and dissolve it in 10mL of ethanol, and simultaneously weigh 0.39g (4.1mmol) of 2-aminopyridine and dissolve it in 10mL of ethanol, and add the latter dropwise to In the ethanol solution of 3,5-dimethyl salicylaldehyde, after stirring and heating to reflux for 6 hours, the ethanol was evaporated under reduced pressure, and recrystallized with 10mL ethanol to obtain the product 3,5-dimethyl salicylaldehyde acetal 2- Aminopyridinium base, the yield is 61.2%.

[0026] Accurately weigh 2.70 g (12.1 mmol) of 3,5-dimethyl salicylaldehyde acetal 2-aminopyridinzanthine and dissolve it in 20 mL of ethanol-water (V: V=4: 1), then add 0.75 g ( 12.1 mmol) boric acid. Control the reflux temperature to 75-80° C., react for 3 hours, filter the obtained solution, extract, place, and precipitate the product with a yield of 46.3%. ...

Embodiment 3

[0029] Example 3: Synthesis of pyridine-2"-amino-3', 5'-diethyl-2'-hydroxybenzyl alcohol borate

[0030] Accurately weigh 0.73g (4.1mmol) of 3,5-diethyl salicylaldehyde and dissolve it in 10mL of ethanol, simultaneously weigh 0.39g (4.1mmol) of 2-aminopyridine and dissolve it in 10mL of ethanol, and add the latter dropwise to In the ethanol solution of 3,5-diethyl salicylaldehyde, heat and reflux under stirring for 4 hours, evaporate the ethanol under reduced pressure, and recrystallize with 10mL ethanol to obtain the product 3,5-diethyl salicylaldehyde acetal 2- Aminopyridinium base, the yield is 56.2%.

[0031] Accurately weigh 3.08 g (12.1 mmol) of 3,5-diethyl salicylaldehyde acetal 2-aminopyridinzanthine and dissolve it in 20 mL of ethanol-water (V: V=4: 1), then add 0.75 g ( 12.1 mmol) boric acid. Control the temperature at 75-80° C., react for 4 hours, filter the obtained solution, extract and place it, and the product is precipitated with a yield of 44.4%.

[0032] v...

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 Pyridine-2''-amino-2'-hydroxybenzene methanol phenylcarbinol boric acid ester compound and a synthetic method thereof. The technical proposal is: the Pyridine-2''-amino-2'-hydroxybenzene methanol phenylcarbinol boric acid ester compound has the following constitutional formula and the synthetic method is: 2-aminopyridine and salicylal derivative are added to ethanol solution and heated for 4-6 hours for reflux in case of stirring, and then ethanol is removed by steaming in case of decompression; the ethanol is used for recrystallization, thus obtaining salicylal derivative condensated-2-aminopyridine schiff base; the boracic acid and the salicylal derivative condensated-2-aminopyridine schiff base are stirred for 2-5 hours at the controlled temperature of 75-80 DEG C in ethanol and aqueous medium, and the obtained solution is filtered, extracted and placed, thus obtaining the precipitated product. The ester terpenoid of the invention features abundant raw materials and simple synthesis.

Description

Technical field: [0001] The invention relates to the field of chemical synthesis, in particular to a pyridine-2"-amino-2'-hydroxybenzyl alcohol borate compound and a synthesis method thereof. Background technique: [0002] Amines, especially secondary amines, are important intermediates in organic synthesis. The synthesis of amines occupies a very important position in the fields of medicinal chemistry and organic synthetic chemistry. Secondary amines are highly polar, difficult to handle, and unstable to oxidation. The research on the synthesis of secondary amines has always been one of the hotspots of synthetic chemists. In 2001, Jung published a review that systematically summarized these works. Since then, researchers have continuously made new progress in the research on the synthesis method of secondary amines, and many new synthesis methods have emerged. [0003] Reductive amination is an important reaction in organic synthesis and one of the important methods for ...

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): C07F5/04
Inventor 葛春华张向东王铁梅张蕊门艳梅王睿
Owner LIAONING 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