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A synthesis method of 3,4-dimethoxy hyacinthin

A technology of dimethoxybenzaldehyde and dimethoxybenzene, applied in 3 fields, can solve the problems of difficult industrialized production operation, increased raw material cost, low yield and the like, and is beneficial to large-scale industrialized production and industrial operation. Simple, high product content

Active Publication Date: 2008-04-16
TIANJIN CENT PHARM CO LTD
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  • Abstract
  • Description
  • Claims
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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

[0026] 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.

[0027] 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

[0029] 16.8g (0.1011mmol) 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, the water layer was extracted with 10ml×3 toluene, washed with saturated aqueous sodium chloride, dried with 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.

[0030] 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 sodium ch...

Embodiment 3

[0032] 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.

[0033] 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 present invention discloses a new synthesis method of 3,4-dimethoxyphenylacetaldehyde, in which 3,4- dimethoxy- benzaldehyde is adopted as the raw material, and TEBA or TBAB adopted is adopted as the transfer catalyst in organic or mixed solvent under alkaline condition, Darzen's condensation reaction is carried out under the condition of the temperature controlled at 10 DEG C to 40 DEG C and the reaction is carried out with the duration roughly within 8 to 72 hours, then hydrolyzation and decarboxylation is carried out in the mixed solvent to obtain 3,4-dimethoxyphenylacetaldehyde. The present invention carries out Darzen's reaction with the phase-transfer catalysis, avoids the substances including expensive potassium tert-butoxide, flammable and explosive sodium, and virulent methyrl, and has a high yield of 3,4- dimethoxy- benzaldehyde with stable content, and simple industrial operation in favor of massive industrialized 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 Applications(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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