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Novel method for preparing Scopoletin

A technology of hydroxycoumarin and organic solvents, which is applied in the field of medicine and can solve the problems of lack of conditions for mass production, high cost, and difficulty in obtaining special raw materials.

Inactive Publication Date: 2009-09-02
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Some of the existing methods for preparing scopolamine require the use of special raw materials that are difficult to obtain, the cost is high, and the reaction yield of some is not very ideal, and the conditions for large-scale preparation are not available.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 2,4-dihydroxy-5-methoxybenzaldehyde:

[0024] 2,4,5-Trimethoxybenzaldehyde (19.6 g, 0.1 mol) in dry dichloromethane (50 mL). Under the condition of 0-5°C, a certain amount of pyridine (25ml) was slowly added dropwise to completely dissolve the solid. After reflux reaction at 40° C. for 5 h, another part of aluminum trichloride (26.7 g, 0.2 mol) in dry dichloromethane (100 ml) was added. After continuing to stir and reflux for 15 hours, cool to room temperature, pour the reaction mixture into 500 g of crushed ice, slowly add 35 ml of concentrated hydrochloric acid while stirring, and wait until the ice in the mixed solution is completely melted, separate the lower organic layer, and wash the water layer with dichloromethane Extracted twice with methane, then backwashed the combined organic layer with water, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and finally recrystallized with toluene to obtain 2,4-dihydrox...

Embodiment 2

[0026] Preparation of 6-methoxy-7-hydroxycoumarin:

[0027] 2,4-Dihydroxy-5-methoxybenzaldehyde (13.44g, 80mmol) and ethyl triphenylphosphonoacetate (36.24g, 104mmol) were dissolved in 250ml of N,N-dimethylaniline, stirred . Under nitrogen protection, the reaction solution was heated at 180° C. for 5 hours, and the reaction solution was vigorously refluxed. Then it was naturally cooled to room temperature, and the formed crystals were filtered out and washed with anhydrous ether to obtain crude product 1 (7.5 g). The filtrate was distilled off the solvent under reduced pressure (N,N-dimethylaniline was recovered) to obtain a brown-black thick liquid, which was extracted with dichloromethane, and 5% dilute hydrochloric acid was added dropwise, and the pH of the upper aqueous layer was measured with pH test paper. Until the upper aqueous solution is slightly acidic to fully remove residual N,N-dimethylaniline. The lower organic layer is separated, and then backwashed with a c...

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PUM

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Abstract

The invention relates to a novel method for preparing Scopoletin, which comprises that: (a) 2,4,5-trimethoxybenzaldehyde and aluminium trichloride are demethylated in an organic solvent to generate 2,4-dihydroxy-5-methoxy benzaldehyde; and (b) under the protection of nitrogen, the 2,4-dihydroxy-5-methoxy benzaldehyde and ethyltriphenylphosphonium acetate undergo a pyroreaction in an organic solvent with high boiling point to generate esculetin-6-methyl ether (the Scopoletin). The preparation method can effectively produce the Scopoletin industrially on a large scale.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new method for preparing scopoletin. Background technique [0002] Scopoletin, also known as scopoletin, scopoletin, scopoletin, scopoletin, etc., belongs to coumarin compounds, and its chemical name is 6-methoxy-7-hydroxycoumarin. The structure is shown in formula I. Scopolamine is mainly found in the roots of Solanaceae scopolamine (Swpolia japonica Maxim.), belladonna (Atropa balladonna L.), and umbrella plant Angelica dahurica Benth.et Hook. Studies have shown that scopoletin has obvious pharmacological activities, such as analgesic, anti-inflammatory, hypotensive, antispasmodic, anti-tumor and prevention of hyperuricemia, etc., and has very important medicinal value. [0003] Formula I [0004] Chinese patent application CN1615847 published in 2005 describes a method for extracting scopolamine from coarse powder of Porana sinensis Hemsl. with ethanol. Ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16A61P29/00A61P9/12A61P35/00A61P19/06
Inventor 周金培魏丽娟戴岳张惠斌蒋企洲
Owner CHINA PHARM UNIV
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