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Synthetic method of 8-isoquinolinol

The technology of a hydroxyisoquinoline and a synthetic method, which is applied in the field of synthesis of isoquinoline compounds, can solve the problems of troublesome post-processing, complicated operation, and low total yield, and achieve convenient operation and post-processing, reasonable process selection, The effect of concise synthetic route

Inactive Publication Date: 2017-07-21
XUZHOU MEDICAL UNIV +1
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Problems solved by technology

[0005] Technical problem to be solved: Aiming at the problems in the prior art such as long synthetic route, low total yield, complicated operation, troublesome post-treatment, extensive use of highly toxic and corrosive chemicals, and unsuitability for large-scale production, the present invention provides a A synthetic method for 8-hydroxyisoquinoline, the synthetic route is simple, the process selection is reasonable, the raw materials are simple and easy to obtain, the operation and post-treatment are convenient, the total yield is high, and it is easy to scale up

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  • Synthetic method of 8-isoquinolinol

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Embodiment 1

[0019] Add 10 g, 61.35 mmol 8-chloroisoquinoline, 0.81 g, 3.07 mmol copper acetylacetonate, 2.71 g, 64.42 mmol lithium hydroxide monohydrate and 0.92 g to a mixed solution of 49.1 mL dimethyl sulfoxide and 12.3 mL water , 3.07 mmol ligand 1,3-bis(4-hydroxy-2,6-dimethylphenyl)urea. Under nitrogen protection, the prepared reaction solution was stirred at 130° C. for 24 hours. After the stirred reaction solution was cooled, the solution was acidified with 2mol / L HCl to pH=5, the mixed solution was extracted with ethyl acetate, the extracted organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and then spun After drying, the crude product was separated by column chromatography to obtain 6.41 g of 8-hydroxyisoquinoline with a total yield of 72%.

[0020] The 1H NMR spectrum of 8-hydroxyisoquinoline is as follows: 1H NMR (400MHZ, DMSO-d6): 6.97(d, 1H), 7.31(d, 1H), 7.54-7.59(m, 1H), 7.62(m ,1H),8.38(m,1H),9.36(m,1H),10.38(m,1H).

[0021] The 8-chlor...

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Abstract

The invention discloses a synthetic method of 8-isoquinolinol, and belongs to the field of synthesis method of isoquinoline compounds. The synthetic method comprises following steps: 8-chloroisoquinoline, copper acetylacetonate, lithium hydroxide monohydrate, and ligand 1,3-bis(4-hydroxyl-2,6-dimethyl phenyl)urea are added into a mixed solution of dimethyl sulfoxide and water; under nitrogen protection, an obtained reaction solution is subjected to heating with stirring until reaction is completed, and pH value is adjusted to 5 with HCl after cooling; an obtained mixed liquid is extracted with ethyl acetate, an obtained organic phase is washed with saturated salt solution, is dried with anhydrous sodium sulfate, and then is subjected to spin drying; and an obtained crude product is subjected to column chromatography separation so as to obtain 8-isoquinolinol. According to the synthetic method, 8-chloroisoquinoline is taken as a raw material; synthesis route is simple; the synthetic method is reasonable; the raw materials are easily available; operation and subsequent treatment are convenient; total yield is as high as 72%; amplify production is convenient to realize; and large-scale production of 8-isoquinolinol can be realized.

Description

technical field [0001] The invention belongs to the field of synthesis methods of isoquinoline compounds, in particular to the synthesis method of 8-hydroxyisoquinoline. Background technique [0002] Isoquinoline compounds are important compounds in organic synthesis and pharmaceutical synthesis, and 8-hydroxyisoquinoline is a typical representative of this type of molecule. A series of novel organic compounds can be synthesized by modifying or derivatizing the functional groups of the intermediates. compound. The latest research shows that these compounds have good biological activity and can be used as a new agent for Helicobacter pylori monotherapy, with strong bactericidal and bacteriostatic effects; they can also be used as antagonists of SNS sodium channels, with analgesic and neuroprotective effects ( WO2005 / 5392A1); in addition, it can also be used in combination with various agents to more effectively treat diseases such as diabetes, neurological disorders and meta...

Claims

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Application Information

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IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 张浩王小东徐卫良徐炜政
Owner XUZHOU MEDICAL UNIV
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