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Method for synthesizing 5,7-dihydroxyflavone

A technique for the synthesis of dihydroxyflavones, which is applied in the field of synthesis of flavonoids, can solve problems such as large environmental pollution, and achieve the effects of less environmental pollution, rich sources of raw materials, and short reaction steps

Inactive Publication Date: 2011-04-13
HANGZHOU FST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction will use chloroacetonitrile with certain toxicity, which will cause great environmental pollution.

Method used

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  • Method for synthesizing 5,7-dihydroxyflavone
  • Method for synthesizing 5,7-dihydroxyflavone
  • Method for synthesizing 5,7-dihydroxyflavone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of ethyl benzoylacetate

[0020] Put drinking water into the reaction kettle, pump in 100kg of ethyl acetoacetate, cool down to 5±5°C, slowly add sodium hydroxide solution dropwise, and keep warm. At the same time, start to add benzoyl chloride dropwise, keep the temperature in the kettle not exceeding 10°C, and keep the pH>11. After the dropwise addition, keep warm for 5 hours. Ammonium chloride was added, and the reaction was maintained at 25±5°C for 8 hours. After completion of the reaction, after-treatment, about 150kg of ethyl benzoyl acetate crude distillate was obtained. Distill once with Roots pump high vacuum, obtain about 133kg light yellow oily liquid. HPLC >97%, yield 90%.

Embodiment 2

[0022] Preparation of ethyl benzoylacetate

[0023] Put drinking water into the reaction kettle, pump in 100kg of ethyl acetoacetate, cool down to 5±5°C, slowly add potassium hydroxide solution dropwise, and keep warm. At the same time, start to add benzoyl chloride dropwise, keep the temperature in the kettle not exceeding 10°C, and keep the pH>11. After the dropwise addition, keep warm for 5 hours. Ammonium chloride was added, and the reaction was maintained at 25±5°C for 8 hours. After completion of the reaction, after-treatment, about 145kg of ethyl benzoyl acetate crude distillate was obtained. Distill once with Roots pump high vacuum, obtain about 125kg light yellow oily liquid. HPLC>97%, yield 84.5%.

Embodiment 3

[0025] Preparation of ethyl benzoylacetate

[0026] Put an appropriate amount of methanol into the reaction kettle, pump in 100kg of ethyl acetoacetate, cool down to 5±5°C, slowly add sodium hydroxide solution dropwise, and keep warm. At the same time, start to add benzoyl chloride dropwise, keep the temperature in the kettle not exceeding 10°C, and keep the pH>11. After the dropwise addition, keep warm for 5 hours. Add ammonium chloride aqueous solution, and keep the reaction at 25±5°C for 8 hours. After completion of the reaction, after-treatment, about 120kg of ethyl benzoyl acetate crude distillate was obtained. Distill once with Roots pump high vacuum, obtain about 108kg light yellow oily liquid. HPLC >97%, yield 73%.

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Abstract

The invention relates to a method for synthesizing flavone compounds, in particular to a method for synthesizing 5,7-dihydroxyflavone. The method comprises the following steps: in the presence of a condensing agent, reacting an active methylene compound (ethyl acetoacetate) with an acylating agent (benzoyl chloride), and importing benzoyl into the active methylene; selectively hydrolyzing the obtained product by utilizing ammonium chloride solution so as to remove acetyl, thus obtaining ethyl benzoylacetate; mixing the obtained intermediate with phloroglucinol to dissolve the obtained intermediate, then warming, vacuumizing and reacting to obtain a crude product; and refining the crude product by utilizing DMF (dimethylformamide) and ethanol so as to obtain the 5,7-dihydroxyflavone. The method provided by the invention has the advantages of rich sources of feed, low cost and short reaction step, and is simple in operation; and meanwhile, through the optimization of reaction conditions, the method also has the advantages of short reaction step, high yield, low cost, less environmental pollution and the like. The products prepared by the method can be used for preparing medicaments and the like.

Description

technical field [0001] The invention relates to a flavonoid compound and a synthesis method, in particular to a synthesis method of 5,7-dihydroxyflavone. technical background [0002] Flavonoids are widely distributed and important polyphenol natural products in plants. They exist in almost all green plants and play an important role in the growth, development, flowering and fruiting of plants and in resisting the invasion of foreign bodies. It has a wide range of pharmacological activities, although it is not as strong as alkaloids, but due to its wide distribution and variety, some compounds are high in plants, and most compounds are easy to obtain in crystal form, so the research on this type of compounds is relatively extensive and in-depth , is an important class of compounds in natural products. [0003] 5,7-dihydroxyflavone belongs to flavonoids, Chinese alias: Ke Yin; isooxyflavone; also known as chrysin, exists in the seeds and stem bark of Oroxylum indicum (L.) Ve...

Claims

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Application Information

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IPC IPC(8): C07D311/30
Inventor 吴永龙徐伟沈学全张伟伟
Owner HANGZHOU FST PHARMA
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