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Synthetic method of 3-bromo-7-methoxyl quinoline

A technology for the synthesis of methoxyquinoline and its synthesis method, which is applied in the field of synthesis of 3-bromo-7-methoxyquinoline, and can solve the problem of instability of 2-bromomalondialdehyde, instability of preparation raw materials, troublesome post-processing, etc. problem, to achieve the effect of solving the instability of raw materials, easy enlargement, convenient operation and post-processing

Inactive Publication Date: 2018-11-02
SUZHOU KANGRUN PHARMA
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  • Claims
  • Application Information

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Problems solved by technology

But, preparation raw material 2-bromomalondialdehyde is particularly unstable, and the yield of this synthetic method is very low, and bibliographical report minimum yield only has 3.8%, in addition, the aftertreatment trouble of this process method
Therefore, in order to overcome the shortcomings of unstable raw materials, low yield, post-processing troubles and not easy to enlarge, it is necessary to develop a synthetic method for 3-bromo-7-methoxyquinoline

Method used

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  • Synthetic method of 3-bromo-7-methoxyl quinoline

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Experimental program
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Embodiment

[0033] The first step: the synthesis of 7-nitroquinoline

[0034] Dichloromethane (4.5L) was added to 7-nitro-1,2,3,4 tetrahydroquinoline (60g, 0.337mol), and dichlorodicyanobenzoquinone (152.9g, 0.6734mol ), stirred at room temperature for 1 h, and suction filtered, and the filter cake was stirred with dichloromethane (500 mL*2) for 5 min, and suction filtered; the combined filtrates were washed with 10% NaOH (500 mL*2), and then washed with saturated NaCl solution (500 mL), Organic phase anhydrous Na 2 SO 4 Dry and concentrate to dryness by rotary evaporation. The concentrated orange-yellow solid was stirred with 250 ml of petroleum ether: ethyl acetate = 5:1 solvent for 30 min, filtered and dried to obtain 7-nitroquinoline (53 g, 90.3%).

[0035] The second step: the synthesis of 3-bromo-7-nitroquinoline

[0036] Glacial acetic acid (350ml) was added to 7-nitroquinoline (50g, 0.287mol), the temperature was raised to 106°C, and N-bromosuccinimide (51.1g, 0.2870mol) was a...

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Abstract

The invention provides a synthetic method of 3-bromo-7-methoxyl quinoline. The synthetic method of 3-bromo-7-methoxyl quinoline comprises the following steps: 1) adding a solvent into 7-nitryl-1,2,3,4-tetrahydroquinoline, adding DDQ and stirring the mixture to react to obtain 7-nitryl quinoline, wherein the molar ratio of 7-nitryl-1,2,3,4-tetrahydroquinoline and DDQ is 1: (1-5); 2) adding the solvent into 7-nitryl quinoline, heating the mixture, adding N-bromo-succinimide to react to obtain 3-bromo-7-nitryl quinoline in an insulating manner; and 3) dissolving 3-bromo-7-nitryl quinoline in thesolvent, adding sodium methylate, and heating the mixture to stir and react to obtain 3-bromo-7-methoxyl quinoline. The synthetic method of 3-bromo-7-methoxyl quinoline is concise in synthetic route,reasonable in process selection, low in raw material cost, simple and easy, convenient to operate and post-treat, high in total yield and easy to amplify.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and relates to a synthesis method of 3-bromo-7-methoxyquinoline. Background technique [0002] 3-Bromo-7-methoxyquinoline is an important pharmaceutical intermediate in medicinal chemistry. The bromine atom at the 3-position is a highly active reaction site, which can undergo transition metal-catalyzed coupling with some fragments or intermediates Reactions, such as Buchwald-Hartwig reaction, Heck reaction, Sonogashira reaction, Still reaction and Suzuki reaction, so as to achieve the purpose of carbon chain extension and structural modification. Studies have shown that a series of compounds synthesized with 3-bromo-7-hydroxyquinoline as the mother nucleus can inhibit the activity of 17β-hydroxysteroid dehydrogenase 1 (17β-HSD1). The main function of 17β-HSD1 is to convert estrone into For functional estradiol (US20100204234). [0003] In addition, a series of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/20
CPCC07D215/20
Inventor 黄家慧徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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