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A synthesis method of 3,4-dimethoxy hyacinthin

A technology of dimethoxybenzaldehyde and dimethoxybenzene, applied in 3 fields, can solve problems such as difficulty in industrialized production operation, unsuitable needs for large-scale industrialized production, increase in cost of raw materials, etc., and is beneficial to large-scale industrialization Production, avoidance of metallic sodium and highly toxic methanol, the effect of simple industrial operation

Active Publication Date: 2009-09-16
TIANJIN CENT PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In USP5057624, Cannata et al. adopt Darzens condensation, alkali hydrolysis, decarboxylation reaction, continuous operation, and mild conditions, but the price of reagents 2-butoxide potassium and 2-butyl chloroacetate is relatively high, resulting in an increase in raw material costs
[0009] The method reported by Jia Shuxiang and Wang Mingliang in "Chemical Times" 2006, 2:21-22 improved Cannata et al.'s Darzens condensation. First, sodium metal was used to prepare sodium methoxide. Under the action of sodium methoxide, 3,4-dimethoxy Phenylacetaldehyde and methyl chloroacetate carry out Darzens condensation, but due to the use of flammable and explosive metal sodium and highly toxic methanol, the industrial production operation is difficult, and the reaction time is long, the yield is low, and it is not suitable for large-scale industrial production needs

Method used

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  • A synthesis method of 3,4-dimethoxy hyacinthin
  • A synthesis method of 3,4-dimethoxy hyacinthin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] With 3,4-dimethoxybenzaldehyde 8.4g (0.0505mmol), methyl chloroacetate 5.2ml (0.0594mmol), potassium carbonate 8.2g (0.0594mmol), dimethylformamide 25ml, TEBA0.4g (0.0018 mmol), added to the reaction flask, stirred and reacted at room temperature for 48 hours, TLC showed that the raw materials disappeared, added 60ml of water and 30ml of dichloromethane, separated into layers, and the aqueous layer was extracted with 10ml×3 dichloromethane, washed with saturated aqueous sodium chloride solution, anhydrous Dry over magnesium sulfate, filter, drop the filtrate into 7.2g potassium hydroxide and 50ml ethanol solution, precipitate solid, stir and react at room temperature for 4 hours, cool to 0°C, filter to obtain potassium salt.

[0028] Add the solid potassium salt into the mixed solution of water, dichloromethane and potassium dihydrogen phosphate, stir at room temperature for 4 hours, separate layers, extract the water layer with 10ml×3 dichloromethane, wash with saturate...

Embodiment 2

[0030] 16.8g (0.10mmol) of 3,4-dimethoxybenzaldehyde, 13.3ml (0.1516mmol) of methyl chloroacetate, 20.9g (0.1516mmol) of potassium carbonate, 25ml of tetrahydrofuran, and 0.9g (0.0040mmol) of TEBA were added Reaction bottle, stirred at room temperature for 24 hours, TLC showed that the raw materials disappeared, added 60ml of water and 30ml of toluene, separated into layers, extracted the water layer with 10ml×3 toluene, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and the filtrate was dropped Put it into 14.4g potassium hydroxide and 50ml ethanol solution, precipitate solid, stir and react at room temperature for 4 hours, cool to 0°C, filter to obtain potassium salt.

[0031] Add the solid potassium salt into the mixed solution of water, dichloromethane and potassium dihydrogen phosphate, stir at room temperature for 4 hours, separate layers, extract the water layer with 10ml×3 dichloromethane, wash with saturated aqueous sod...

Embodiment 3

[0033] 4.2g (0.0253mmol) of 3,4-dimethoxybenzaldehyde, 2.9ml (0.0328mmol) of methyl chloroacetate, 2.2g (0.0393mmol) of potassium hydroxide, 12.5ml of dimethylformamide, dichloromethane 12.5ml, TBAB 0.4g (0.0012mmol), add to the reaction bottle, 40 ℃, stirring reaction for 72 hours, TLC shows that the raw material disappears, add 60ml of water and 20ml of dichloromethane, separate layers, the water layer is extracted with 10ml×3 dichloromethane , washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was dropped into 3.6g potassium hydroxide and 50ml ethanol solution to precipitate a solid, stirred and reacted at room temperature for 4 hours, cooled to 0°C, filtered to obtain potassium salt.

[0034] Add the solid potassium salt into the mixed solution of water, dichloromethane and potassium dihydrogen phosphate, stir at room temperature for 4 hours, separate layers, extract the water layer with 10ml×3 dichloro...

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Abstract

The invention discloses a synthesis method of 3,4-dimethoxyphenylacetaldehyde, which uses 3.4-dimethoxybenzaldehyde as raw material, adopts phase transfer catalyst TEBA or TBAB, and organic solvent in alkaline condition Or in a mixed solvent, through Darzen's condensation reaction, the reaction temperature is controlled at 10-40 ° C, and the reaction time is about 8-72 hours, and then hydrolyzed and decarboxylated in a mixed solvent to obtain 3,4-dimethoxyphenyl ethyl aldehyde. In the present invention, the Darson condensation reaction is prepared by a phase-transfer catalytic method, avoiding expensive potassium tert-butoxide, flammable and explosive metal sodium and highly toxic methanol, and the prepared 3,4-dimethoxybenzene The acetaldehyde yield is high, the content is stable, and the industrial operation is simple, which is more conducive to large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of related drug intermediates, in particular to a synthesis method of 3,4-dimethoxyphenylacetaldehyde. technical background [0002] Verapamil Hydrochloride Tablets (Verapamil Hydrochloride Tablets), also known as: verapamil is a derivative of papaverine, is a calcium ion influx inhibitor (slow channel blocker), in the heart, calcium ion influx is inhibited It reduces the self-discipline of sinoatrial node and atrioventricular node, and slows down the conduction, but rarely affects the conduction of atrium, ventricular muscle and atrioventricular bypass. Inhibition of calcium ion influx also reduces the utilization of calcium ions in the excitation-contraction coupling of cardiomyocytes, affects the activity of contractile proteins, weakens myocardial contraction, reduces cardiac work, and reduces myocardial oxygen consumption. Inhibition of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/277C07C45/48
Inventor 孟庆礼杨冠宇宋凤武
Owner TIANJIN CENT PHARM CO LTD
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