Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 7,8-dihydroxy flavone

A dihydroxyflavone and compound technology, applied in the field of preparation of 7,8-dihydroxyflavone, can solve the problems of 7,8-DHF industrial production limitation, high price, etc., and achieve easy industrial implementation, simple operation and low price Effect

Pending Publication Date: 2020-06-19
湖北万知化工医药股份有限公司 +1
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthetic method of 7,8-DHF reported in the literature is mainly based on 7-hydroxyflavone or 2,3,4-trihydroxyacetophenone as raw materials, and these two raw materials are rare and expensive in the market. -The industrial production of DHF has certain limitations

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 7,8-dihydroxy flavone
  • Preparation method of 7,8-dihydroxy flavone

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0028] A kind of preparation method of 7,8-dihydroxyflavone described in this specific embodiment, its steps are as follows:

[0029] 1. Pyrogallol uses boron trifluoride ether as a solvent, acetic acid as an acylating reagent, undergoes Friedel-Crafts acylation reaction under the protection of an inert gas at a relatively low temperature, and the reactant is filtered, washed with alkali, and dried by suction to obtain Compound dhf1. Among them, the molar ratio of pyrogallol, acetic acid and boron trifluoride ether is 1:6-9:2-4.

[0030] 2. The compound dhf1 was mixed with benzyl chloride under the protection of an inert gas, potassium iodide was added, dbu was added dropwise to react at 110°C, the reaction solution was poured into ice water and stirred, and solids were precipitated, filtered by suction, washed with water and dried to obtain the compound dhf2 , The molar ratio of dhf1 to DBU and benzyl chloride is 1:5-7:5-7.

[0031] 3. The compound dhf2 is mixed with acetic...

Embodiment 1

[0036] A preparation method of 7,8-dihydroxyflavone, the steps are as follows:

[0037] (1) Synthesis of compound dhf1

[0038] Put 600g of glucinol and 2L of acetic acid into a 5L three-necked bottle, under the protection of Ar, control the temperature below 50°C, add 1.8L of boron trifluoride diethyl ether dropwise, and control the temperature at 90-100°C for 6-8h. After the reaction was completed, the crude product was directly obtained by suction filtration, and the crude product was washed with saturated sodium bicarbonate. Suction filtration and drying yielded 8 kg of a brownish-yellow solid product with a melting point of 63-64°C. The product was confirmed by NMR with a yield of 90%.

[0039] (2) Synthesis of compound dhf2

[0040] Under the protection of argon, put 1kg dhf-1 and 3kg benzyl chloride into a 5L three-necked bottle, add 50g of catalytic amount of potassium iodide dropwise to the mixed solution, and then add 3.6kg dbu dropwise to it under the control temp...

Embodiment 2

[0050] A preparation method of 7,8-dihydroxyflavone, the steps are as follows:

[0051] (1) Synthesis of compound dhf1

[0052] Put 600g of glucinol and 2L of acetic acid into a 5L three-neck bottle, under the protection of Ar, control the temperature below 60°C, add 1.9L of boron trifluoride diethyl ether dropwise, and control the temperature at 90°C for 6h. After the reaction was completed, the crude product was directly obtained by suction filtration, and the crude product was washed with saturated sodium bicarbonate. After suction filtration and drying, 8.5 kg of a brownish-yellow solid product with a melting point of 63° C. was obtained, and the product was confirmed by NMR with a yield of 89.50%.

[0053] (2) Synthesis of compound dhf2

[0054] Under the protection of argon, put 1kg dhf-1 and 3kg benzyl chloride into a 5L three-necked flask, add 50g of catalytic amount of potassium iodide dropwise to the mixed solution, and then add 4.0kg dbu dropwise to the mixed solu...

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a preparation method of 7,8-dihydroxy flavone, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps:by taking pyrogallol as a raw material, introducing an acetyl group to synthesize DHF1; protecting three phenolic hydroxyl groups to synthesize DHF2; selectively reducing the ortho-hydroxyl group of the acetyl group to synthesize DHF3; carrying out an aldol condensation reaction on DHF3 and benzaldehyde to prepare DHF4; carrying out a cyclization reaction under the condition of iodine catalysis toobtain DHF5; and finally carrying out a hydrolysis reaction to generate the final product. The method is simple and convenient to operate, reasonable in reaction process, low in production cost, goodin product quality, free of environmental pollution and suitable for industrial production, wherein the content of the product is higher than 98%.

Description

technical field [0001] The invention relates to a preparation method of 7,8-dihydroxyflavone, which belongs to the technical field of synthesis of pharmaceutical intermediates. Background technique [0002] 7,8-dihydroxyflavone is a kind of flavonoid. Studies have shown that 7,8-DHF is a specific agonist of tyrosine kinase B (TrkB) receptors, which can activate TrkB receptors and play an important role in neuroprotection, such as improving learning and memory and antidepressant. . 7,8-DHF is the first reported drug that can simulate the effect of BDNF, and can enter the brain tissue through the blood-brain barrier, and can improve a variety of neurodegenerative diseases and other abnormal brain functions. In addition, 7,8-DHF also has the functions of dilating blood vessels, lowering blood pressure, anti-oxidation and anti-inflammation that other flavonoids share. Its market prospect and economic benefits therefore have great potential. [0003] The synthetic method of 7...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杜小兰蔡丽华
Owner 湖北万知化工医药股份有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com