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Method for preparing 9, 10-bi (N-(2, 3-dihydroxypropyl) propionamido) anthracene

A technology of propionamide group and dihydroxypropyl group, which is applied in the field of preparation of 9,10-dipropionamide group) anthracene, can solve the problems of long synthesis process, unfavorable for industrialized production, complicated operation and the like

Inactive Publication Date: 2019-05-24
GANNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a long synthesis process, and uses dangerous reactants or reagents such as sodium metal, concentrated sulfuric acid, etc. that are flammable, explosive, corrosive, and highly toxic. The operation is complicated and the yield is low, which is very unfavorable for industrial production.

Method used

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  • Method for preparing 9, 10-bi (N-(2, 3-dihydroxypropyl) propionamido) anthracene
  • Method for preparing 9, 10-bi (N-(2, 3-dihydroxypropyl) propionamido) anthracene
  • Method for preparing 9, 10-bi (N-(2, 3-dihydroxypropyl) propionamido) anthracene

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preparation example Construction

[0022] The invention provides a method for preparing 9,10-bis(N-(2,3-dihydroxypropyl)propionamido)anthracene, comprising the following steps:

[0023] (1) Mix 9,10-dibromoanthracene, ethyl acrylate, the first palladium catalyst, ligand, base and the first organic solvent, and perform a Heck reaction to obtain 9,10-bis(3-ethyl acrylate) Anthracene;

[0024] (2) 9,10-bis(3-acrylic acid ethyl)anthracene obtained in the step (1) is mixed with a second palladium catalyst, a reducing agent and a second organic solvent, and hydrogenation reaction is carried out to obtain 9,10 - bis(3-propionoethyl)anthracene;

[0025] (3) Mix the 9,10-bis(3-propionate ethyl)anthracene obtained in the step (2) with 3-amino-1,2-propanediol and an alcohol solvent, and carry out amine transesterification to obtain the 9,10-bis(N-(2,3-dihydroxypropyl)propionamido)anthracene.

[0026] The present invention mixes 9,10-dibromoanthracene (compound 1), ethyl acrylate, the first palladium catalyst, a ligand,...

Embodiment 1

[0054] A preparation method of 9,10-di(N-(2,3-dihydroxypropyl)propionamido)anthracene (DHPA):

[0055] (1) At room temperature, 9,10-dibromoanthracene (3.36g, 10mmol, 1.0eq), ethyl acrylate (10g, 100mmol, 10.0eq), Pb(OAc) 2 (246.9mg, 1.10mmol, 0.11eq), tris(o-tolyl)phosphine (669.6mg, 2.20mmol, 0.22eq) dissolved in 28mL (200mmol, 20eq) of triethylamine and 100mL of N,N-dimethyl In formamide (DMF), under nitrogen protection, reflux at 120° C. for 5 h. After the reaction solution was cooled, the Heck reaction solution was washed with saturated brine (the volume ratio of saturated brine to Heck reaction solution was 1000mL: 100mL), and extracted with ethyl acetate (the volume ratio of ethyl acetate to Heck reaction solution was 1000mL: 100mL), the organic phase was collected and dried with anhydrous sodium sulfate (the dosage ratio of anhydrous sodium sulfate and organic phase was 33g: 1000mL) for 10min, concentrated at 30°C with a rotary evaporator to obtain a crude product; th...

Embodiment 2

[0059] A preparation method of 9,10-di(N-(2,3-dihydroxypropyl)propionamido)anthracene (DHPA):

[0060] (1) At room temperature, 9,10-dibromoanthracene (3.36g, 10mmol, 1.0eq), ethyl acrylate (5g, 50mmol, 5.0eq), Pb(OAc) 2(112.2mg, 0.5mmol, 0.05eq), tris(o-tolyl)phosphine (304.4mg, 1.0mmol, 0.1eq) dissolved in 14mL (100mmol, 10eq) of triethylamine and 100mL of N,N-dimethyl In formamide (DMF), under nitrogen protection, reflux at 120° C. for 5 h. After the reaction solution is cooled, wash the Heck reaction solution with saturated saline (the volume ratio of saturated saline to Heck reaction solution is 1000mL: 100mL), and wash with ethyl acetate (the volume ratio of ethyl acetate to Heck reaction solution is 1000mL: 100mL ) extraction, the collected organic phase was dried with anhydrous sodium sulfate (the dosage ratio of anhydrous sodium sulfate and organic phase is 33g: 1000mL) for 15min, and concentrated at 40°C with a rotary evaporator to obtain a crude product; the crude ...

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Abstract

The invention provides a 9, 10-bi (N-(2, 3-dihydroxypropyl) propionamido) anthracene (DHPA), and relates to the technical field of chemical synthesis. The method comprises the following steps: mixing9, 10-dibromoanthracene, ethyl acrylate, a first palladium catalyst, a ligand, alkali and a first organic solvent to carry out Heck reaction to obtain 9, 10-bi (3-ethyl acrylate group) anthracene (compound 2); mixing the compound 2 with a second palladium catalyst, a reducing agent and a second organic solvent, and performing hydrogenation reaction to obtain 9, 10-bi (3-ethyl propionate group) anthracene (compound 3); mixing the compound 3 with a 3-amino-1, 2- propylene glycol and alcohol solvent for carrying out amine ester exchange reaction to obtain the final product DHPA. When the method is used for preparing the DHPA, common reagents are adopted, and the cost of raw materials is low; the preparation process is short, and the yield is as high as 85%; the method is safe and convenient to operate, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 9,10-bis(N-(2,3-dihydroxypropyl)propionamido)anthracene. Background technique [0002] Singlet oxygen (singlet oxygen, 1 o 2 ) is one of the important members of the active oxygen family, and plays a very important role in many fields such as organic synthesis, photodynamic therapy and biological processes. However, due to its high activity and extremely short lifetime (3.5 μs in water, 67.0 μs in heavy water), it is very difficult to detect singlet oxygen. Among them, using chemical probes to capture singlet oxygen and detecting singlet oxygen through the corresponding absorption or fluorescence changes before and after capture is a very fast and effective method. Currently commercially available such singlet oxygen scavengers mainly include 1,3-diphenylisobenzofuran (DPBF), 9,10-diphenylanthracene (9,10-diphenylanthrancene, DPA), 9,10-anth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/22
Inventor 王建国姜国玉王强范小林
Owner GANNAN NORMAL UNIV