2-quinolinone compound and preparation method and application thereof

A technology for quinolinones and compounds, which is applied in the application of detecting Hg2+, in the field of preparation of 2-quinolinone compounds, can solve the problems of complicated operation, cumbersome sensor preparation method, etc., and achieves simple detection process, convenient preparation, low cost effect

Inactive Publication Date: 2014-02-12
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some sensors have been applied to the detection of mercury ions in cells and organisms, there are still some shortcomings such as cumbersome preparation methods, complicated operations, and sometimes the need for masking agents to eliminate...

Method used

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  • 2-quinolinone compound and preparation method and application thereof
  • 2-quinolinone compound and preparation method and application thereof
  • 2-quinolinone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 3-(2-benzimidazolyl)-6,7-difluoro-2-quinolinone (BIDFQ)

[0031] (1) In a 250mL reaction flask, add 38.7mL (0.5mol) DMF, cool in an ice-water bath to 0°C, add 116.3mL (1.25mol) phosphorus oxychloride dropwise under stirring, and control the dropping rate to keep the temperature of the reaction system At 0±2°C, continue the reaction at low temperature for 0.5 hours after the addition is complete, then add 42.75g (0.25mol) of 3,4-difluoroacetanilide, heat to 70°C and keep the reaction for 16 hours. After cooling, the reaction solution was poured into crushed ice to precipitate a yellow solid, which was filtered, washed with water, and dried to obtain 9 g of 2-chloro-6,7-difluoro-3-quinolinecarbaldehyde, with a yield of 15.8%.

[0032] (2) In a 50mL reaction flask, add 25mL of 70% acetic acid aqueous solution and 2.275g (10mmol) of 2-chloro-6,7-difluoro-3-quinolinecarbaldehyde, and heat to reflux for 6 hours. Cool, filter, wash with water, and dry to obtain...

Embodiment 2

[0040] Preparation of 3-(2-benzimidazolyl)-6,7-difluoro-2-quinolinone (BIDFQ)

[0041] (1) The preparation of 2-chloro-6,7-difluoro-3-quinolinecarbaldehyde is the same as in Example 1;

[0042] (2) The preparation of 3-formyl-6,7-difluoro-2-quinolinone is the same as in Example 1;

[0043] (3) In a 10mL reaction flask, add 5mL absolute ethanol and 209mg (1mmol) 3-formyl-6,7-difluoro-2-quinolinone, start stirring, then add 108mg (1mmol) phthalate Amine and 17.2 mg p-toluenesulfonic acid, and then heated to reflux for 7 hours. Cool, filter, and recrystallize with acetone to obtain 184 mg of 3-(2-benzimidazole)-6,7-difluoro-2-quinolinone, with a yield of 62%.

Embodiment 3

[0045] Preparation of 3-(2-benzimidazolyl)-6,7-difluoro-2-quinolinone (BIDFQ)

[0046] (1) The preparation of 2-chloro-6,7-difluoro-3-quinolinecarbaldehyde is the same as in Example 1;

[0047] (2) The preparation of 3-formyl-6,7-difluoro-2-quinolinone is the same as in Example 1;

[0048] (3) In a 10mL reaction flask, add 5mL absolute ethanol and 209mg (1mmol) 3-formyl-6,7-difluoro-2-quinolinone, start stirring, then add 108mg (1mmol) phthalate Amine and 18.6 mg of boric acid were then heated to reflux for 10 hours. Cool, filter, and recrystallize with acetone to obtain 166 mg of 3-(2-benzimidazole)-6,7-difluoro-2-quinolinone, with a yield of 56%.

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Abstract

The invention provides a 2-quinolinone compound and a preparation method and application thereof. The 2-quinolinone compound is 3-(2-benzimidazolyl)-6, 7-difluoro-2-quinolinone. The preparation method comprises the following steps: taking 3, 4-difluoro acetanilide as an initial raw material, reacting with POC13 (phosphorus oxychloride) and DMF (dimethyl formamide) to obtain 2-chlorine-6, 7-difluoro quinoline-3-formaldehyde, then hydrolyzing to generate 3-aldehyde group-6, 7-difluoro-2-quinolinone, then reacting with o-phenylenediamine to obtain the 2- quinolinone compound. The 2-quinolinone compound can be used as a fluorescent probe for quantitative detection of the content of Hg<2+>, and shows high sensitivity and selectivity, the detection process is simple and rapid, and the detection result is accurate.

Description

technical field [0001] The invention belongs to the technical field of synthesis of heterocyclic organic compounds, in particular to a preparation method of 2-quinolinone compounds and its performance in detecting Hg 2+ aspects of application. Background technique [0002] Mercury is a chemical substance with severe physiological toxicity. Once it enters the organism, it will accumulate in the organism, resulting in chronic poisoning, damage to the brain, kidney, stomach and intestinal tract, and even death. In recent years, due to the widespread use of mercury and mercury salts in industry, mercury pollution in the environment has become serious. Therefore, Hg 2+ Quantitative detection is very important in drug, food, clinical and environmental testing. [0003] Currently, the commonly used Hg 2+ The detection methods are: spectrophotometry, atomic emission spectrometry, atomic absorption spectrometry, hydride generation-atomic fluorescence spectrometry, X-ray fluoresce...

Claims

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Application Information

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IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06C09K2211/1029C09K2211/1044G01N21/6402
Inventor 张永斌郝俊生霍方俊阴彩霞钞建宾刘滇生
Owner SHANXI UNIV
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