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Synthesis method of 3-bromoquinoline compound

A synthesis method and technology for aniline compounds, applied in the direction of organic chemistry and the like, can solve the problems of incapable of industrialized production, unobtainable raw materials, difficult separation, etc., and achieve the effects of few reaction steps, cheap raw materials, and easy purification.

Pending Publication Date: 2019-05-31
YA THERAPEUTICS INC
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The raw materials of this method are not easy to obtain, and concentrated acid is used for diazotization, which leads to a lot of waste water and great pollution
[0015] The synthesis reports of these 3-bromoquinoline compounds either require high temperature, complex products, and difficult separation; or the raw materials are not easy to obtain, the waste water is large, the pollution is large, and industrial production cannot be carried out.

Method used

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  • Synthesis method of 3-bromoquinoline compound
  • Synthesis method of 3-bromoquinoline compound
  • Synthesis method of 3-bromoquinoline compound

Examples

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Embodiment 1

[0025] Embodiment 1: the synthesis of 3-bromoquinoline

[0026] 1. Synthesis of Intermediate 3

[0027] Add 100g of compound 1 to 96ml of water, slowly add 5.4ml of hydrochloric acid and 105.6g of liquid bromine dropwise at 0°C, stir overnight at room temperature, spin off the water at 45°C, filter, and wash the solid with PE:EA times, dried to obtain 50g intermediate 3.

[0028] 2. Synthesis of Intermediate 4

[0029] Add 16.8g NaOH to 400ml of water, then slowly add 60g of intermediate 3, spin off the water under reduced pressure until solids precipitate, then add 1L of cold acetone, stir overnight at 4 degrees, filter, and dissolve the solids in 500ml of cold water The acetone was washed twice, and the solid was pulled dry with an oil pump to obtain 68g of intermediate 4.

[0030] 3. Synthesis of 3-bromoquinoline 1

[0031] Add 100g of intermediate 3 and 53.8g of anthranilic acid to 500ml of ethanol, then slowly add 150ml of 30% hydrobromic acetic acid dropwise, heat to...

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Abstract

The invention provides a synthesis method of a 3-bromoquinoline compound. The invention belongs to the field of medical chemical synthesis. The synthesis method comprises the following steps: taking 1, 1, 3, 3-tetramethoxypropane 2 as a raw material to react with bromine to obtain an intermediate 3, obtaining an intermediate 4 from the intermediate 3 under the action of alkali, and reacting the intermediate 4 with a substituted aniline compound to obtain the 3-bromoquinoline compound 1, wherein R1 and R2 are selected from any one of hydrogen, alkyl, alkoxy, halogen, ester, nitro, trifluoromethyl, trifluoromethoxy, dimethylamino, acetyl and methylthio. The synthesis method of the 3-bromoquinoline compound has the advantages of few reaction steps, simplicity in operation, cheap and easily available raw materials, high yield, easiness in purification and easiness in amplified production.

Description

Technical field: [0001] The present invention The present invention relates to a synthetic method of a pharmaceutical intermediate, in particular, the present invention relates to a synthetic method of 3-bromoquinoline compounds. [0002] technical background [0003] Quinoline ring is a kind of heterocycle with strong biological activity, especially halogenated quinoline compounds have a broad spectrum of biological activity. Compounds containing quinoline rings are widely used in the prevention and treatment of diseases such as malaria, ulcers, cancer, HIV, and schizophrenia. Compounds containing quinoline rings also have antifungal, anti-tuberculosis, and anti-filariasis properties. Some of these compounds have been commercialized, such as quinine and chloroquine, which were earlier drugs used by humans to prevent and treat malaria. Many small molecule drugs can also improve physiological activity and enhance drug efficacy through quinoline group modification. In pes...

Claims

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Application Information

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IPC IPC(8): C07D215/18
Inventor 曾兆森梁永宏
Owner YA THERAPEUTICS INC
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