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Method for preparing isoproterenol hydrochloride

A technology of isoproterenol hydrochloride and epinephrine, applied in the field of medicine, can solve the problems of difficult treatment of phosphorus-containing wastewater, great harm to human body, low reaction yield, etc., achieve obvious economic and environmental benefits, and facilitate industrial production , the effect of less dosage

Active Publication Date: 2017-08-04
SHANDONG KEYUAN PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In this route, catechol and monochloroacetic acid are obtained through the Friedel-Crafts reaction under the condition of phosphorus oxychloride to obtain chloroacetyl catechol (I). The phenomenon of material condition occurs from time to time, and a large amount of hydrogen chloride gas is produced in the reaction, which is extremely difficult to handle
And need to use phosphorus oxychloride and monochloroacetic acid, phosphorus oxychloride and monochloroacetic acid are very harmful to the human body, both are also very corrosive, and the phosphorus-containing wastewater after the reaction is also extremely difficult to treat

Method used

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  • Method for preparing isoproterenol hydrochloride
  • Method for preparing isoproterenol hydrochloride
  • Method for preparing isoproterenol hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Preparation of 2-amino-1-(3,4-dihydroxyphenyl)-ethanone:

[0032] Add 1L of 1,2-dichloroethane into the reaction bottle, add 330g of zinc chloride when the temperature is lowered to 10-15°C, stir for 20 minutes after the addition, add catechol 110g (1.0mol) in batches to the reaction In the bottle, continue to stir for 30 minutes after the addition, then raise the temperature to 70°C, add dropwise a solution of 75g (1.0mol) of glycine in 1,2-dichloroethane, heat up to reflux for 12 hours after the addition, and cool down after the reaction to room temperature, add dilute hydrochloric acid to quench, stir at 20-30°C for 2-3 hours, collect the solid by filtration, adjust the pH of the solid to about 6.7 with aqueous sodium bicarbonate solution, filter, collect the solid, and dry to obtain the product 2- Amino-1-(3,4-dihydroxyphenyl)-ethanone 125.3 g, yield 75.02%.

[0033] (2) Preparation of isoproterenol ketone body hydrochloride

[0034] Add 250g of 95% ethanol an...

Embodiment 2

[0038] (1) Preparation of 2-amino-1-(3,4-dihydroxyphenyl)-ethanone:

[0039] Add 1L of 1,2-dichloroethane into the reaction bottle, add 450g of zinc chloride when the temperature is lowered to 10-15°C, stir for 20 minutes after the addition, add catechol 110g (1.0mol) in batches to the reaction In the bottle, continue to stir for 30 minutes after the addition, then raise the temperature to 70°C, add dropwise a solution of 78.6g (1.05mol) of glycine in 1,2-dichloroethane, and raise the temperature to reflux for 20 hours after the completion of the reaction. Cool down to room temperature, add dilute hydrochloric acid to quench, stir at 20-30°C for 2-3 hours, collect the solid by filtration, adjust the pH of the solid to about 6.8 with aqueous sodium bicarbonate solution, filter, collect the solid, and dry to obtain product 2 -Amino-1-(3,4-dihydroxyphenyl)-ethanone 128.3 g, yield 76.82%.

[0040] (2) Preparation of isoproterenol ketone body hydrochloride

[0041] Add 250g of 95...

Embodiment 3

[0045] (1) Preparation of 2-amino-1-(3,4-dihydroxyphenyl)-ethanone:

[0046] Add 1L of 1,2-dichloroethane into the reaction bottle, add 550g of zinc chloride when the temperature is lowered to 10-15°C, stir for 20 minutes after the addition, add catechol 110g (1.0mol) in batches to the reaction In the bottle, continue to stir for 30 minutes after the addition, then raise the temperature to 70°C, add dropwise a solution of 82.5g (1.1mol) of glycine in 1,2-dichloroethane, after the addition, raise the temperature to reflux for 20 hours, after the reaction Cool down to room temperature, add dilute hydrochloric acid to quench, stir at 20-30°C for 2-3 hours, and collect the solid by filtration. Adjust the pH of the solid to about 7 with aqueous sodium bicarbonate solution, filter, collect the solid, and dry to obtain 131.6 g of the product 2-amino-1-(3,4-dihydroxyphenyl)-ethanone with a yield of 78.8% .

[0047] (2) Preparation of isoproterenol ketone body hydrochloride

[0048]...

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Abstract

The invention relates to a method for preparing isoproterenol hydrochloride. The method comprises the following steps: (1) preparation of 2-amino-1-(3, 4-dihydroxy phenyl)-ethanone; (2) preparation of isoproterenol ketone hydrochloride; and (3) preparation of isoproterenol hydrochloride. The method disclosed by the invention adopts a reaction system of glycine and zinc chloride instead of a reaction system of monochloro acetic acid and phosphorus oxychloride, so that the method has the advantages that the environmental protection cost is reduced; the reaction yield is increased; the industrial production is benefited; the reaction condition is mild; the catalyst quantity is little; and the process is simple. Compared with conventional synthetic processes, the method disclosed by the invention has obvious economic benefit and environmental benefit.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to a preparation method of a medicinal compound, in particular to a preparation method of isoproterenol hydrochloride. Background technique [0002] Isoproterenol hydrochloride, English name: Isoprenaline Hydrochloride, molecular formula: C11H18ClNO3, chemical name: 4-[(2-isopropylamino-1-hydroxy)ethyl]-1,2-benzenediol hydrochloride. Isoproterenol hydrochloride, also known as Chuanxiding, Zhichuanling, is an adrenaline-mimicking drug that relaxes the bronchi. It is used to suppress the attack of bronchial asthma, and it is also used for acute and chronic pulmonary asthma of allergic asthma. Its chemical structural formula is as follows: [0003] [0004] The current production of isoproterenol hydrochloride mainly takes the following reaction route: [0005] Catechol and monochloroacetic acid are reacted by Friedel-Crafts reaction under the action of phosphorus oxychloride to ob...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/60
CPCC07C213/00C07C221/00C07C215/60C07C225/16
Inventor 伦立军任小亮王广洪吴玉良
Owner SHANDONG KEYUAN PHARMA
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