Method for preparing 9-oxo-10(9H)-acridineacetic acid

A technology of acridone acetic acid and o-chlorobenzoic acid, applied in directions such as organic chemistry, can solve problems such as low product yield, severe reaction, pollution and the like

Active Publication Date: 2013-11-20
ZHENGZHOU SIGMA CHEM
View PDF2 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method for preparing acridone acetic acid has problems such as large solvent consumption, low yield, violent reaction and serious pollution.
For example, when the condensation reaction synthesizes the intermediate N-phenylanthranilic acid, the base usually used in the literature is a metal hydroxide (such as: NaOH), which easily leads to a strong alkalinity in the system and difficult control of the pH value. The commonly used The catalyst is copper powder,

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The process includes the following steps:

[0026] ① Condensation reaction: Add 2kg DMSO into the reaction flask with thermometer and reflux tube, add 2kg of o-chlorobenzoic acid (a), 1.3kg of cesium carbonate, CuFe 2 o 4 0.12kg of magnetic powder and 1.4kg of aniline (b), the temperature of the system was directly raised to 100°C, at this time the system began to reflux to react, followed by TCL, the reaction was complete after 3 hours, and the heating was stopped. Add a certain amount of cooling water to lower the temperature of the system to 70°C, add 0.2kg of activated carbon and 0.2kg of sodium sulfide nonahydrate, continue to stir until the system is uniform, then filter, and then add concentrated hydrochloric acid to adjust the pH of the filtrate to about 1. At this time, products are precipitated. The product was filtered, washed with water and dried to obtain a white solid powder c2.62kg for use, with a yield of 96%;

[0027] ② Cyclization reaction: Add 26kg ...

Embodiment 2

[0031] The process includes the following steps:

[0032] ① Condensation reaction: Add 2.5kg DMSO into the reaction flask with thermometer and reflux tube, add 2kg of o-chlorobenzoic acid (a), 1.2kg of potassium carbonate, CuFe 2 o 4With 0.1kg of magnetic powder and 1kg of aniline (b), the temperature of the system was directly raised to 102°C. At this time, the system was refluxed and started to react, followed by TCL. After 3 hours, the reaction was complete, and the heating was stopped. Add a certain amount of cooling water to lower the temperature of the system to 70°C, add 0.2kg of activated carbon and 0.2kg of sodium sulfide nonahydrate, continue to stir until the system is uniform, then filter, then add concentrated hydrochloric acid to adjust the pH of the filtrate to 1, at this time a product is precipitated, the The product was filtered, washed with water, and dried to obtain a white solid powder c2.65kg for use, with a yield of 97%;

[0033] ② Cyclization reaction...

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 preparing 9-oxo-10(9H)-acridineacetic acid, and belongs to the field of organic synthesis. The method comprises the following steps: (1) under the effects of a metal carbonate, a catalyst and a solvent, performing a condensation reaction on o-chlorobenzoic acid (a) and aniline (b) to prepare an intermediate c; (2) under the effects of toluene and p-toluenesulfonic acid, performing a cyclization reaction on the intermediate c by refluxing and dehydrating to prepare an intermediate d; (3) dissolving the intermediate d in dimethyl formamide , successively adding 60% NaH, KI and ethyl chloroacetate, reacting at room temperature to obtain a wet intermediate e; and (4) hydrolyzing the wet intermediate d with NaOH to obtain a crude product f, and refining the crude product f to obtain the 9-oxo-10(9H)-acridineacetic acid product. The method has the advantages of low cost consumption, small pollution during reaction, smooth and easy-controlling reaction and high product yield, and has better industrial application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing acridoneacetic acid. Background technique [0002] Acridone derivatives have become a research hotspot in the field of medicine in recent years due to their good antibacterial, anti-inflammatory, anti-malarial and anti-cancer activities. Electrostatic attraction binds to DNA, and some 9-aminoacridine derivatives have been clinically used as DNA intercalation reagents due to their good pharmacological and biological activities. As an important pharmaceutical intermediate, acridone acetic acid has received more and more attention. [0003] The traditional method for preparing acridone acetic acid has problems such as large solvent consumption, low yield, violent reaction and serious pollution. For example, when the condensation reaction synthesizes the intermediate N-phenylanthranilic acid, the base usually used in the literature is a metal hydr...

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): C07D219/06
Inventor 武小军王建莉郝家金杨广远
Owner ZHENGZHOU SIGMA CHEM
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