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

Method for synthesizing 3,4-dimethoxyphenyl acetonitrile

A synthesis method and compound technology, applied in 3 fields, can solve the problems of harsh reaction conditions, unsuitable dehydration, and high cost, and achieve the effects of short production cycle, simple operation and good quality.

Active Publication Date: 2009-07-08
TIANJIN CENT PHARM CO LTD
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The dehydration of hydroxy compounds often uses strong acid catalysts, but it is not suitable for the dehydration of aldoximes, because Beckman rearrangement will occur to obtain formamide, and if the dehydration continues, isocyanides will be obtained; instead of acid halides or acid anhydrides, such as acetic acid / acetic anhydride / acetic acid Sodium dehydration consumes too much and the cost is too high; dehydration with active esters, amides and organic salts, methoxy will participate in the reaction and generate by-products; organic salt reactions require strict anhydrous conditions, and the reaction conditions are harsh; low-priced phosphorus Compound requires CCl 4 Participation, the toxicity is too high; only strong alkaline reagents have low cost, simple operation, and are conducive to industrial production
[0009] In "Chemical Reagents" 2000, 22(2), 128 "Synthesis of Anhydrous Acetaldoxime", "Chemistry and Adhesion" 2005, 27(1), 61-62, "Improvement of the Synthesis Method of Acetaldoxime" In, "Journal of Nanning Normal College", 2004, 4, "Carrier Base KOH / Al 2 o 3 In "Study on the Dehydration of Citric Oxime", the dehydration of strong alkaline reagents is used to prepare nitriles, but the methods mentioned all require rectification to obtain nitriles.

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 synthesizing 3,4-dimethoxyphenyl acetonitrile
  • Method for synthesizing 3,4-dimethoxyphenyl acetonitrile
  • Method for synthesizing 3,4-dimethoxyphenyl acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 3, the preparation of 4-dimethoxyphenylacetaldehyde [B]

[0041] 52.4g (0.2mol) 3-(3,4-dimethoxyphenyl)-2',3'-epoxypropionic acid potassium salt [A], 32.6g (0.24mol 1.2 times) KH 2 PO 4 , 100ml of purified water, 100ml of toluene into the reaction flask, 15 ℃, react for 3 hours, separate the toluene layer, extract the water layer with 20ml of toluene, combine the toluene layer, anhydrous MgSO 4 After drying, a toluene solution of 3,4-dimethoxyphenylacetaldehyde [B] was obtained, HPLC 99.2%.

Embodiment 2

[0043] Preparation of 3,4-Dimethoxyphenylacetaldoxime [C]

[0044] With the toluene solution of 3,4-dimethoxyphenylacetaldehyde [B] in embodiment 1, 16.8g (0.2mol1 times) NaHCO 3 , 13.9g (0.2mol 1 times) HONH 3 Put Cl into the reaction bottle, react at 15°C for 3 hours, add 100ml of purified water, separate the toluene layer, extract the water layer with 20ml of toluene, combine the toluene layers, and anhydrous MgSO 4 After drying, a toluene solution of 3,4-dimethoxyphenylacetaldoxime [C] was obtained, HPLC 99.3%.

Embodiment 3

[0046] Preparation of 3,4-dimethoxyphenylacetonitrile [D]

[0047] With the toluene solution of 3,4-dimethoxyphenylacetaldoxime [C] in embodiment 2, 1.7g (0.03mol 0.15 times) KOH, 1.3g (0.004mol 0.02 times) tetrabutylammonium bromide ( TBAB), 10ml DMSO was added to the reaction flask, refluxed and separated for 30 minutes, after cooling down, 100ml purified water was added, adjusted to pH=7 with glacial acetic acid, the toluene layer was separated, the water layer was extracted with 20ml toluene, the toluene layers were combined, and purified with 100ml Washed, anhydrous MgSO 4 Dry and concentrate to dryness under reduced pressure to obtain 32.7 g of yellow oil, add 65 ml of absolute ethanol, crystallize at -5 ° C for 8 hours, filter, and rinse with ice ethanol to obtain 3,4-dimethoxyphenylacetonitrile [D ]30.2g, properties: white solid, HPLC 99%, melting point 63°C-65°C, yield 85.24%.

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 synthesizing 3,4-dimethoxy benzyl cyanide, which comprises three steps of decarboxylation reaction, aldoxime reaction and dehydration reaction, namely performing decarboxylation on 3-(3,4-dimethoxyphenyl)-2',3'-epoxy-potassium propionate in water to prepare 3,4- dimethoxy phenylacetaldehyde, using a solvent such as ether, alkyl chloride, benzene, toluene for extraction, directly adding sodium bicarbonate and hydroxylamine hydrochloride for aldoxime reaction, and finally adding a phase-transfer catalyst and alkali for direct reflux and water division and obtaining finished products through recrystallization in ethanol. The preparation method has simple reaction procedure, removes harmful substances such as cyanide, improves the yield, reduces the cost, and is more suitable for industrial mass production.

Description

technical field [0001] The invention relates to a synthesis method of 3,4-dimethylbenzyl nitrile, which belongs to the technical field of medicine and chemical industry. Background technique [0002] Verapamil Hydrochloride, also known as Isoptin, chemical name: α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl Base]-3,4-dimethoxy-α-isopropylphenylacetonitrile hydrochloride. Verapamil hydrochloride is a derivative of papaverine, which is an inhibitor of calcium ion influx (slow channel blocker). Inhibition of calcium ion influx in the heart reduces the automaticity of sinoatrial node and atrioventricular node , the conduction slows down, but rarely affects the conduction of atrium, ventricular muscle and atrioventricular bypass. The inhibition of calcium ion influx also reduces the utilization of calcium ions in the excitation-contraction coupling of cardiomyocytes and affects the activity of contractile proteins. Myocardial contraction weakens, heart work decreases, ...

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): C07C255/37C07C253/00
Inventor 孟庆礼杨冠宇宋风武
Owner TIANJIN CENT PHARM CO LTD
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