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Preparation method of acridone N-alkylation derivative

An acridone and alkylation technology, which is applied in the field of preparation of acridone N-alkylated derivatives, can solve the problems of limited application of catalysts, equipment corrosion, and excessive waste liquid, and achieve good industrial application value and reaction The effect of mild conditions and safe operation

Active Publication Date: 2015-05-06
ZHENGZHOU SIGMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method of preparing N-alkylated derivatives of acridone is mainly through the substitution reaction of acridone in an alkylating agent and solvent (such as DMF) and under the condition of an inorganic strong base (such as NaH). , this type of reaction has the disadvantages of severe corrosion to equipment, large amount of waste liquid, serious pollution, low production efficiency and incomplete reaction.
Although the application of phase transfer catalysts has greatly facilitated the progress of such reactions, the recovery of catalysts and the use of toxic solvents have greatly limited the further application of this technology.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] This synthetic method comprises the steps:

[0018] At room temperature, add 29.2g [Pmim]OH ionic liquid and 19.5g acridone successively into a three-necked flask with a condensing reflux device, stir evenly, add 11.3g chloroacetic acid, control the temperature at 25°C, stir and react for 12h, then let stand at room temperature , filtered, and then washed the filter cake with 25ml of methanol and dried to obtain 24.2g of acridoneacetic acid (yield: 95.7%). 1H-NMR (CDCl 3 , δ, ppm): 7.28-7.69 (m, 8H, Ar’, H), 11.98 (s, 1H, OH, carboxylic acid), 2.52 (s, 2H, -CH).

Embodiment 2

[0020] This synthetic method comprises the steps:

[0021] At room temperature, add 35.2g [Emim]OH ionic liquid and 19.5g acridone into a three-necked flask with a condensing reflux device, stir evenly, add 15.4g 3-chloropropionic acid, control the temperature at 50°C and stir for 8 hours. Stand still, filter, then wash the filter cake with 25ml of methanol and dry to obtain 25.6g of acridone propionic acid (yield: 95.9%). 1H-NMR (CDCl 3 , δ, ppm): 7.21-7.59 (m, 8H, Ar', H), 11.96 (s, 1H, OH, carboxylic acid), 2.46 (m, 2H, -CH), 2.40 (m, 2H, -CH ).

Embodiment 3

[0023] This synthetic method comprises the steps:

[0024] At room temperature, add 69g [Omim]OH ionic liquid and 19.5g acridone successively into a three-necked flask with a condensing reflux device, stir evenly, add 17.4g sodium chloroacetate, control the temperature at 35°C, stir and react for 8h, then let stand at room temperature , filter, then wash the filter cake with 30ml of methanol and dry to obtain 27.2g of acridone sodium acetate (yield: 94.1%). 1H-NMR (CDCl 3 , δ, ppm): 7.27-7.68 (m, 8H, Ar’, H), 2.40 (s, 2H, -CH).

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PUM

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Abstract

The invention discloses a preparation method of acridone N-alkylation derivative, which comprises the following steps: adding an alkaline ion liquid and acridone into a three-neck flask provided with a condensation reflux unit at room temperature, stirring uniformly, adding halide, stirring to react at 20-50 DEG C for 6-12 hours, standing at room temperature, filtering, washing the filter cake with methanol, and drying to obtain the acridone N-alkylation derivative product. The method has the advantages of mild reaction conditions, high yield and recyclable ion liquid, is safe and convenient to operate, and has favorable industrialized application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of N-alkylated derivatives of acridone. technical background [0002] Acridone derivatives have good antibacterial, anti-inflammatory, anti-malarial and anti-cancer activities, and have become a research hotspot in the field of medicine in recent years. This type of compound has a rigid planar structure of a macrocyclic conjugated system, which can be absorbed by embedding or electrostatic Attracting the combination with DNA, the N-alkylated derivatives of acridone have received more and more attention as an important pharmaceutical intermediate. [0003] The traditional method of preparing N-alkylated derivatives of acridone is mainly through the substitution reaction of acridone in an alkylating agent and solvent (such as DMF) and under the condition of an inorganic strong base (such as NaH). , This type of reaction has the disadvantages of sev...

Claims

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Application Information

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IPC IPC(8): C07D219/06
CPCC07D219/06
Inventor 王建莉杨勇郝家金秦峰李义波胡孝伦赵萍萍王娅娟
Owner ZHENGZHOU SIGMA CHEM
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