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Synthetic method of 6-hydroxyl-2(1H)-quinolinone compound

A synthetic method and technology of quinolinone, applied in the direction of organic chemistry, etc., to achieve the effect of low production cost, cheap raw materials, and easy availability of raw materials

Active Publication Date: 2012-12-12
苏州卫优知识产权运营有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthetic route is relatively direct, the total yield is only 17%.

Method used

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  • Synthetic method of 6-hydroxyl-2(1H)-quinolinone compound
  • Synthetic method of 6-hydroxyl-2(1H)-quinolinone compound
  • Synthetic method of 6-hydroxyl-2(1H)-quinolinone compound

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Experimental program
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Embodiment 1

[0029] The preparation of embodiment 1 gemini surface active agent

[0030] 1) Alkylation Add 16.8g (0.1mol) of diphenylmethane, anhydrous AlCl 3 13g, fully stirred to disperse the catalyst evenly, at 45-50°C, add 34g (0.2mol) of dodecene dropwise, the dropping time is controlled at 20-30min to complete the dropwise addition, then gradually raise the reaction temperature to 70°C, and keep No change, react for 8 hours, after the reaction, adjust the reaction solution to neutral, extract with toluene, dry over anhydrous magnesium sulfate, filter, concentrate to obtain the alkylated product for the next step of sulfonation;

[0031] 2) Sulfonation In a four-necked reaction flask equipped with an electric stirrer, a thermometer, a reflux condenser, and a dropping funnel, add the alkylated product obtained above, and add 24 g (0.2 mol) of chlorosulfonic acid dropwise under vigorous stirring. ), the dropping time is 1h, the reaction temperature is controlled at 20-25°C, and the rea...

Embodiment 2

[0033] Example 2: Preparation of 6-hydroxyl-2(1H)-quinolinone compound

[0034] In a 150ml three-necked flask, add 3.27g (0.3mol) of 4-hydroxyaniline, 5.3g (0.32mol) of cinnamoyl chloride, and 9.8g of the gemini surfactant prepared by the method in Example 1, and react under stirring at 100°C for 10 hours. After the completion, the reaction solution was cooled to room temperature (25°C) and extracted three times with 30 mL of toluene, the toluene layers were combined, concentrated under reduced pressure until no toluene flowed out, and the concentrate was recrystallized with industrial methanol to obtain 1.2 g of a white solid, namely 6-hydroxy- 2(1H)-Quinolinone compound, yield 61%, m.p.>300℃. IR(KBr):3108,2852,1658,1629,1429,1298cm -1 . 1H NMR (DMSO-d 6 )δ: 6.48 (1H, d, J=9.52, H-3), 7.16~7.25 (3H, m, ArH), 7.81 (1H, d, J=9.52, H-4), 9.46 (1H, s, OH), 11.64 (1H, s, H-1).

Embodiment 3

[0035] Example 3: Preparation of 6-hydroxyl-2(1H)-quinolinone compound

[0036] In a 150ml three-necked flask, add 3.27g (0.3mol) of 4-hydroxyaniline, 7.5g (0.45mol) of cinnamoyl chloride, and 33g of the gemini surfactant prepared by the method in Example 1, and react at 150°C for 10 hours while stirring, and the reaction ends The reaction solution was extracted three times with 30 mL of toluene, the toluene layers were combined, concentrated until no toluene flowed out, and the concentrate was recrystallized with industrial methanol to obtain 1.1 g of a white solid, namely 6-hydroxy-2(1H)-quinolinone compound. The rate is 59%.

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Abstract

The invention discloses a synthetic method of a 6-hydroxyl-2(1H)-quinolinone compound, comprising the following steps of: mixing 4-hydroxy aniline and cinnamoyl chloride, performing a reaction with stirring under the action of a gemini surfactant at the temperature of 50-150 DEG C for 1-20 h, and carrying out post-processing on a reacting liquid after the reaction, so as to obtain the 6-hydroxyl-2(1H)-quinolinone compound. The synthetic method provided by the invention is simple, has an advantage of cheap and easily available raw materials, is environmentally friendly, requires low cost, and is suitable for industrial operation.

Description

(1) Technical field [0001] The invention relates to a method for catalytically synthesizing 6-hydroxyl-2(1H)-quinolinone compounds in a diionic surfactant system. (2) Background technology [0002] 6-Hydroxy-2(1H)-quinolinone compounds are platelet cAMP-specific phosphodiesterase (PDE) inhibitors, which can effectively inhibit platelet aggregation. Since cAMP PDE also exists in cardiac muscle and vascular smooth muscle, its inhibitors At the same time, it can enhance myocardial contractility and dilate blood vessels. Therefore, many 2(1H)-quinolinone compounds have different degrees of cardiotonic and antihypertensive effects, and 6-hydroxy-2(1H)-quinolinone compounds have a good effect on inhibiting platelet aggregation. It is of great significance to the prevention and treatment of cardiovascular diseases such as myocardial infarction and stroke. [0003] Gemini surfactants are surfactants with a special structure of two hydrophilic groups and two lipophilic groups, whic...

Claims

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Application Information

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IPC IPC(8): C07D215/22
Inventor 裴文杨振平孙莉王勤邓琼余长泉孙孟展
Owner 苏州卫优知识产权运营有限公司
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