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A kind of preparation method of 3,4-two (2-methoxyethoxy) ethyl benzoate

A technology of ethyl dihydroxybenzoate and methoxyethoxy, which is applied in the field of drug synthesis and can solve problems such as not being environmentally friendly

Active Publication Date: 2021-06-11
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Considering that solvents such as DMF, acetone or acetonitrile are used in the prior art, the reaction involving solvents is not environmentally friendly

Method used

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  • A kind of preparation method of 3,4-two (2-methoxyethoxy) ethyl benzoate
  • A kind of preparation method of 3,4-two (2-methoxyethoxy) ethyl benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 36.4g ethyl 3,4-dihydroxybenzoate, 82.4g potassium carbonate, 6.0g 4-dimethylaminopyridine, 145.6g 1-chloro-2-methoxyethane into a dry and clean 500ml reaction bottle and stir Raise the temperature to 90-95°C, reflux and keep it warm, after the reaction is completed, cool down to 20-30°C, add water and stir, let stand to separate layers, extract the water layer once, combine the organic layers, distill and evaporate, and cool down. Add isopropanol and water, filter with suction, rinse the filter cake with isopropanol and water, drain the wet product, and dry it in vacuum to obtain 57g of the product, with a yield of 95% and a purity of 99% by HPLC.

Embodiment 2

[0032] Add 36.4g ethyl 3,4-dihydroxybenzoate, 82.4g potassium carbonate, 4.0g 4-dimethylaminopyridine, 145.6g 1-chloro-2-methoxyethane into a dry and clean 500ml reaction bottle and stir Raise the temperature to 85-90°C, reflux and keep it warm, after the reaction is completed, cool down to 20-30°C, add water and stir, let stand to separate layers, extract the water layer once, combine the organic layers, distill and steam, and cool down. Add isopropanol and water, filter with suction, rinse the filter cake with isopropanol and water, drain the wet product, and dry it in vacuum to obtain 57g of the product, with a yield of 95% and a purity of 99% by HPLC.

Embodiment 3

[0034] Put 36.4g of ethyl 3,4-dihydroxybenzoate, 82.4g of potassium carbonate, 145.6g of 1-chloro-2-methoxyethane into a dry and clean 500ml reaction bottle, stir and raise the temperature to 85-90°C, and keep the temperature under reflux After the reaction is completed, cool down to 20-30°C, add water and stir, let stand to separate layers, extract the water layer once, combine the organic layers, distill, evaporate, and cool down. Add isopropanol and water, filter with suction, rinse the filter cake with isopropanol and water, drain the wet product, and dry it in vacuum to obtain 54 g of the product, with a yield of 90% and a purity of 97% by HPLC.

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Abstract

The invention belongs to the field of drug synthesis, and relates to a preparation method of an anticancer drug intermediate, in particular to a preparation method of ethyl 3,4-bis(2-methoxyethoxy)benzoate. This preparation method has research reports in many documents or patents, but all need the participation of organic solvents such as acetonitrile, acetone or DMF. The present invention does not need to use the solvent in the existing documents or patents, but can obtain products with high yield and purity, is a green and environment-friendly preparation method, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a preparation method of an anticancer drug intermediate, in particular to a preparation method of ethyl 3,4-bis(2-methoxyethoxy)benzoate. Background technique [0002] Ethyl 3,4-bis(2-methoxyethoxy)benzoate, the structural formula is as follows: [0003] , [0004] It is an intermediate in the synthesis of anticancer drugs, such as erlotinib hydrochloride. [0005] One of the reaction routes is as follows: [0006] . [0007] The second reaction route is as follows: [0008] . [0009] In the prior art, the preparation route of 3,4-two (2-methoxyethoxy) ethyl benzoate is as follows: [0010] . [0011] Among them, potassium carbonate is mostly used as an acid-binding agent. For example, in the international patent application WO2005012264, potassium carbonate is used as the acid-binding agent, and DMF is used as the solvent. For example, in Molecules, 11(4), 286-297; ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/92C07C67/31
CPCC07C67/31C07C67/54C07C69/92
Inventor 李桂民叶美其石德送徐建康蒋志强黄忠林
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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