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Simple and efficient ambroxol synthesis method

A synthesis method and a technology for ambromine are applied in the field of preparation of known organic compounds, and can solve the problems of difficult control of reaction conditions, reduced yield of side reactions, complicated operations, etc., so as to reduce the generation of organic by-products and improve the yield of products. and purity, the effect of reducing pollution

Active Publication Date: 2012-02-15
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main disadvantage of the above method is that the route is long, the operation is complicated, more highly polluting reagents are involved, and the reaction conditions are not easy to control, resulting in too many unnecessary side reactions and reducing the yield

Method used

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  • Simple and efficient ambroxol synthesis method

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Effect test

Embodiment 1

[0021] At room temperature, in a 100 mL three-neck flask, add 1.5 g of o-nitrobenzaldehyde (10 mmol), 35 mL of 80% ethanol solution (500 mmol), and raise the temperature to 50 °C while stirring, and wait until the o-nitrobenzaldehyde is completely After dissolving, add 2.8 g of reduced iron powder (50 mmol) and 3 drops (1 drop is about 0.05 mL) of concentrated hydrochloric acid, pour out the reaction solution after reacting for 30 min, filter it twice, and add the obtained filtrate to a 100 mL three-necked flask 20 mL of ethanol (350 mmol) was added, and 1.6 g of bromine (10 mmol) was added dropwise with stirring at 20 °C. After 15 min, 3 mL of 30% hydrogen peroxide (100 mmol) was added dropwise. ), after the dropwise addition was completed, reacted for 20 min, after the reaction, the reaction solution was added to 200 mL of saturated sodium bicarbonate solution, fully stirred, and then filtered to obtain the crude product 3,5-dibromo-2-aminobenzaldehyde solid 2.36 g; In a 100...

Embodiment 2

[0023] At room temperature, in a 100 mL three-necked flask, add 1.5 g of o-nitrobenzaldehyde (10 mmol), 38.8 mL of 80% ethanol solution (550 mmol), and raise the temperature to 50 °C while stirring, and wait for the o-nitrobenzaldehyde to After all dissolved, add 3.9 g of reduced iron powder (70 mmol) and 3 drops of concentrated hydrochloric acid, pour out the reaction solution after reacting for 30 min, filter with suction twice, add the obtained filtrate into a 100 mL three-necked flask, and add 28 mL Ethanol (400 mmol), stirring at 20 °C, added dropwise 2.1 g of bromine (13 mmol), 15 min to complete the dropwise addition, and then added dropwise 4.5 mL of 30% hydrogen peroxide (150 mmol), after the dropwise addition was completed, After the reaction was completed, the reaction solution was added to 200 mL of saturated sodium bicarbonate solution, stirred thoroughly, and then filtered to obtain 2.61 g of the crude product 3,5-dibromo-2-aminobenzaldehyde as a solid; in a 100 m...

Embodiment 3

[0025]At room temperature, in a 100 mL three-necked flask, add 1.5 g of o-nitrobenzaldehyde (10 mmol), 42.5 mL of 80% ethanol solution (600 mmol), and raise the temperature to 60 °C while stirring, and wait for the o-nitrobenzaldehyde to After all dissolved, add 5.6 g of reduced iron powder (100 mmol) and 3 drops of concentrated hydrochloric acid, pour out the reaction solution after reacting for 30 min, and after suction filtration twice, add the obtained filtrate into a 100 mL three-necked flask, and then add 28 mL Ethanol (400 mmol), stirring at 20 °C, added dropwise 2.1 g of bromine (13 mmol), 15 min to complete the dropwise addition, and then added dropwise 4.5 mL of 30% hydrogen peroxide (150 mmol), after the dropwise addition was completed, After the reaction was completed, the reaction solution was added to 200 mL of saturated sodium bicarbonate solution and stirred thoroughly, and then filtered to obtain 2.51 g of the crude product 3,5-dibromo-2-aminobenzaldehyde as a ...

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Abstract

The invention discloses a simple and efficient ambroxol synthesis method. In the method, a target product is obtained by three unit reactions, namely reduction, bromination and reductive amination. The method comprises the following specific ways: reacting based on o-nitrobenzaldehyde as a raw material and ethanol as a solvent in the presence of iron powder and trace concentrated hydrochloric acid so as to generate o-aminobenzaldehyde; brominating o-aminobenzaldehyde in the presence of bromine and hydrogen peroxide to obtain 3,5-dibromo-2-aminobenzaldehyde; reacting 3,5-dibromo-2-aminobenzaldehyde with trans-p-aminocyclohexanol in methanol for a while and then adding sodium borohydride for reaction so as to produce ambroxol; and finally, extracting out the target product through rotary evaporation. According to the invention, the bromination process is carried out under the mild reaction condition and has short reaction time and mild reaction condition; and 30% hydrogen peroxide and bromine are utilized to replace the traditional bromine salt, thereby improving the utilization rate of bromine, reducing the generation of organic byproducts and reducing pollution to environment.

Description

technical field [0001] The present invention relates to a kind of preparation method of known organic compound, is exactly a kind of simple and efficient synthesis method of ammonium bromide. Background technique [0002] Ambroxol (Ambroxol), the chemical name is trans-4-[[(2-amino-3,5-dibromophenyl)methyl]amino]cyclohexanol, it is a new expectorant, used for acute , Chronic respiratory diseases, especially the expectorant treatment of chronic bronchitis. Ambromide is less toxic and has a strong effect of eliminating phlegm and improving lung function. The melting point is 233~234°C, and its molecular formula is C 13 h 18 Br 2 N 2 O, the relative molecular mass is 375.98. The structural formula of ammonium bromide is: [0003] [0004] About the synthesis route of ambromide all is to comprise three main parts of synthesis of benzene ring precursor, cyclohexanol precursor and the synthesis of the two. The synthesis methods in the prior art include: using o-nitrotol...

Claims

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Application Information

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IPC IPC(8): C07C215/44C07C213/08
Inventor 彭新华赵胜楠马嫣琼
Owner NANJING UNIV OF SCI & TECH
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