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Synthetic method of hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound

A technology of quinolinones and synthesis methods, applied in the direction of organic chemistry, etc., can solve the problems of complex post-treatment process and environmental impact, and achieve the effect of simple synthesis method, low cost, and cheap and easy-to-obtain 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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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional synthesis method has a great impact on the environment, and the post-treatment process is complicated, so the development of green chemical synthesis technology has broad application prospects

Method used

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  • Synthetic method of hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound
  • Synthetic method of hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound
  • Synthetic method of hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound

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Experimental program
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Embodiment 1

[0021] The preparation of embodiment 1 gemini surface active agent

[0022] 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;

[0023] 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

[0025] Example 2 Preparation of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone

[0026] In a 150mL three-neck flask, add 10.9g (0.1mol) of p-hydroxyaniline, 109g of the gemini surfactant prepared by the method in Example 1, and 12.7g (0.1mol) of propionyl chloride, and stir and react at 110°C for 10 hours. The reaction solution was cooled to room temperature (25°C), and then extracted three times with 20 mL of toluene. The extract was concentrated under reduced pressure until no solvent flowed out. The concentrate was recrystallized with industrial methanol and dried to obtain 14.2 g of white solid, namely 6-hydroxy-3, 4-Dihydro-2(1H)-quinolinone, yield 87%, m.p.235~237℃. MS m / z: 163 (M + ); IR (KBr): 3214, 1652, 1504, 1397, 1290, 1253, 949, 815, 779cm -1 ; 1 HNMRδ: 2.34~2.49(2H), 2.74~2.78(2H), 6.52~6.66(3H), 8.90(1H), 9.70(1H)ppm.

Embodiment 3

[0027] Example 3 Preparation of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone

[0028] In a 150mL three-necked flask, add 10.9g (0.1mol) of m-hydroxyaniline, 109g of the gemini surfactant prepared by the method in Example 1, and 12.7g (0.1mol) of propionyl chloride, and stir and react at 130°C for 12 hours. Other operations are the same In Example 2, 13.7 g of white solid was obtained, namely 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, the yield was 84%, m.p.228-230°C. MS m / z: 163 (M + ); IR (KBr): 3279, 1657, 1605, 1523, 1397, 1192, 866, 837, 805cm -1 . 1 HNMRδ: 2.39(2H), 2.73(2H), 6.3(2H), 6.9(1H), 9.24(1H), 9.93(1H) ppm.

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Abstract

The invention discloses a synthetic method of a hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound, comprising the following steps of: mixing hydroxy-substituted aniline and propionyl chloride; reacting under the action of a gemini surfactant as shown in the formula (II) at the temperature of 100-150 DEG C for 1-20 h; and carrying out post-processing on the reaction solution after the reaction so as to obtain the hydroxy-substituted-3,4-dihydro-2(1H)-quinolinone compound. The synthetic method provided by the invention is simple, has advantages of cheap and easily available raw materials, good yield, low cost and repeatedly usable reaction system, and is suitable for industrial operation.

Description

(1) Technical field [0001] The invention relates to a method for catalytically synthesizing a hydroxyl-substituted-3,4-dihydro-2(1H)-quinolinone compound in a dual-ionic surfactant system. (2) Background technology [0002] Hydroxyl-substituted-3,4-dihydro-2(1H)-quinolinone compounds have certain physiological activities and are platelet cAMP (cyclic adenosine monophosphate)-specific phosphodiesterase (PDE-Ⅲ or Ⅳ subtype) Inhibitors can effectively inhibit platelet aggregation. Since cAMP-PDE also exists in myocardial and vascular smooth muscle, its inhibitors can also enhance myocardial contractility and dilate blood vessels. Therefore, most hydroxyl groups replace -3,4-dihydro-2(1H) - Quinolinone compounds have different degrees of cardiotonic and antihypertensive effects, and are widely used in the treatment of cardiovascular diseases. However, the traditional synthesis method has a great impact on the environment, and the post-treatment process is complicated, so the de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22C07D215/26
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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