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Preparation method of indanylidene compound

The technology of a compound and indanedione is applied in the field of preparation of indanedione compounds, which can solve the problems of complicated operation, environmental pollution, long reaction route and the like, and achieve the effects of simple operation steps, environmental friendliness and high product quality.

Inactive Publication Date: 2012-11-21
CHENGDU KAOENSI SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As more and more attention is paid to environmental protection, this synthetic route will produce a large amount of spent acid and spent alkali, which has the problem of environmental pollution, and the operation is cumbersome and the reaction route is long. It is urgent to find a new synthetic route and method.

Method used

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  • Preparation method of indanylidene compound
  • Preparation method of indanylidene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0020] According to the above synthetic route, in the reaction bottle, 30g of raw material compound (2) (produced by Hebei Anping County Chemical Factory, product batch number 200910) was added into 180g 20% ​​H 2 SO 4 Stir in the aqueous solution, and dropwise add 45g of 20% H 2 SO 4 A solution in which 30.7 g of sodium dichromate was dissolved in the solution (the molar ratio of the oxidizing agent to the raw material (2) was 0.9:1). After dropping, warm up to room temperature. Stir the reaction for 4 hours, and measure the end point of the reaction with starch-potassium iodide test paper. The reactant was filtered to obtain the intermediate compound (3) filter cake. The filter cake is directly dissolved in 400ml water without purification and contains Ca(OH) 2 In 15g of alkaline aqueous solution, the Ph value is 8-10. Heat up to 50°C, then add 23g Ca(OH) 2 , and dropwise added 17.2g of chloroacetone (B) (the molar ratio of chloroacetone to the raw material compound (...

Embodiment 2

[0024] Add 30g raw material compound (2) (source is the same as embodiment 1, hereinafter the same) in reaction flask, 46g H 2 O, 80%H 2 SO 4 66g. The reaction solution was cooled to 10°C, and Na was added dropwise 2 Cr 2 o 7 Solution 84g (Na 2 Cr 2 o 7 37.5g, H 2 O 46g) (the molar ratio of oxidant and raw material (2) is 1.1:1), the temperature is maintained at 10-12°C, after the dropwise addition is completed, the temperature is raised to 65°C for 1-2h, and the reaction end point is measured with starch-potassium iodide test paper. After the reaction, cool to room temperature and filter to obtain the filter cake of intermediate compound (3). The filter cake was directly added to 400ml of water, heated to 50°C, and adjusted to pH 8-9 with NaOH aqueous solution. Add Ca(OH) 2 26g, heat the solution to about 55°C and add 18g of chloroacetone (B) dropwise under stirring (the molar ratio of chloroacetone to raw material compound (2) is 1.7:1), raise the temperature to ...

Embodiment 3

[0026] Add raw material compound (2) 30g and 20%H in the reaction flask 2 SO 4 Stir 180g, add dropwise 45ml of aqueous solution containing 30.7g of sodium dichromate (the molar ratio of oxidizing agent and raw material (2) is 0.9:1) at 2 Afterwards, the temperature was raised to 80° C. and 16 g of chloroacetone (B) was added dropwise (the molar ratio of chloroacetone to the raw material compound (2) was 1.5:1), kept for 5 hours, and the end point of the reaction was detected by TLC. After the reaction, the temperature was lowered to 20°C, HCl was added dropwise until pH = 2, cooled, filtered, and dried to obtain 33.8g of compound (4), mp.121-124°C, yield 78%.

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Abstract

A preparation method of an indanylidene compound (1) is disclosed. The indanylidene compound (1) is obtained through reacting a precursor compound (4) with phthalic anhydride (C). The preparation method is characterized in that the preparation method comprises the following steps: oxidizing a raw material delta 2,2'-bis-indoline-3,3'-dione (2) in the presence of an acidic aqueous solution with the pH value of less than 1 and an oxidant (A), filtering the reactant, dissolving the obtained intermediate compound (3) in an alkaline aqueous solution with the pH value of 8-10, reacting with chloroacetone (B) to obtain the precursor compound (4), and further reacting with the phthalic anhydride (C) to obtain the indanylidene compound (1). The synthetic route of the preparation method is shown in the specification.

Description

technical field [0001] The invention relates to a preparation method of indenediones, in particular to a preparation method of 2-(3-hydroxy-2-quinolyl)-1,3(2H)-indenediones. Background technique [0002] 2-(3-Hydroxy-2-quinolinyl)-1,3(2H)-indanedione is a commonly used chemical raw material with a long history of application. The currently reported synthesis routes include: o-nitrobenzaldehyde as a raw material through reduction, cyclization, and condensation reaction, or o-isocyanate toluene as a raw material through chlorination, hydrolysis, cyclization, and condensation. Now it is more common to use oxime acetanilide as a raw material to prepare anilinoglyoxaldoxime (C 8 h 8 o 2 N 2 ), and then cyclized to obtain the intermediate 2,3-dihydroindoline diketone, which is finally prepared by condensation reaction with chloroacetone and phthalic anhydride. As more and more attention is paid to environmental protection, this synthetic route will produce a large amount of s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/20
Inventor 郑虎翁玲玲
Owner CHENGDU KAOENSI SCI & TECH
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