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A kind of preparation and purification method of O-substituted hydroxylamine fluorescence derivatization reagent

A technology of fluorescent derivatization and purification method, which is applied in the field of preparation and purification of O-substituted hydroxylamine fluorescent derivatization reagents, can solve problems such as reduced reactivity, and achieve the effects of product stability, improved detection sensitivity and high reactivity.

Inactive Publication Date: 2019-02-26
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As the number of double bonds conjugated to the aldehyde group increases, its reactivity decreases

Method used

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  • A kind of preparation and purification method of O-substituted hydroxylamine fluorescence derivatization reagent
  • A kind of preparation and purification method of O-substituted hydroxylamine fluorescence derivatization reagent
  • A kind of preparation and purification method of O-substituted hydroxylamine fluorescence derivatization reagent

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specific Embodiment 1

[0028] Below with 1,2-dichloroethane (simultaneously as reaction solvent) is an example to illustrate content of the present invention:

[0029] a) Add 5g of carbazole, 0.96g of tetrabutylammonium bromide and 50mL of 1,2-dichloroethane to a round bottom flask equipped with a magnetic stirrer, and add dropwise with a dropping funnel while stirring 60g of 50% KOH aqueous solution, then heated up to 90°C and reacted for 6 hours; after the reaction, the unreacted 1,2-dichloroethane was removed by rotary evaporation to obtain a brown solid, which was washed with water, filtered, and dried to obtain a light brown powder Solid, unpurified intermediate 1.

[0030] b) Add intermediate I, 5.35g of N-hydroxy-5-norbornene-2,3-diimide and 4.14g of potassium carbonate obtained in the previous step into a round-bottomed flask, and then add an appropriate amount of N,N-di Methylformamide, preferably submerged in solids, was reacted in a magnetic stirrer at 75°C for 10 hours; after the reacti...

specific Embodiment 2

[0034] Taking 1,4-dichlorobutane as an example, using tetrahydrofuran as a solvent, the content of the present invention is illustrated:

[0035] a) Add 5g carbazole, 0.96g tetrabutylammonium bromide, 10mL1,4-dichlorobutane, and 30mL tetrahydrofuran as the reaction solvent to the round-bottomed flask on the magnetic stirrer. Add 60g of 50% KOH aqueous solution to the funnel drop by drop, after the dropwise addition, heat up to 50°C and react for 2 hours; after the reaction, add water and ethyl acetate, shake well, stand to separate layers, separate the ethyl acetate layer with anhydrous Drying over sodium sulfate, rotary evaporation to remove the solvent to obtain a solid, and drying to obtain a powdery solid, which is unpurified intermediate I.

[0036] b) Add intermediate I, 5.35g N-hydroxyl-5-norbornene-2,3-diimide and 4.14g potassium carbonate obtained in the previous step into a round bottom flask, and then add an appropriate amount of N,N- Dimethylformamide, preferably ...

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Abstract

The invention relates to a preparing and purifying method for O-substituted hydroxylamine fluorescence derivatization reagents. Tetra-n-butylammonium bromide and potassium hydroxide are adopted as catalysts. The method includes reacting carbazole and alpha,omega-dihaloalkane to obtain an intermediate I that is 9-(omega-chloroalkyl)-9H-carbazole or 9-(omega-bromoalkyl)-9H-carbazole, reacting the intermediate I with N-hydroxy-5-norbornene-2,3-dicarboximide in dimethylformamide under catalysis of potassium carbonate to obtain an intermediate II that is (3aR,4R,7S,7aS)-2-((9H-carbazole-9-yl)alkoxy)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione, purifying the intermediate II through column chromatography, reacting the intermediate II with hydrazine hydrate to obtain a target product that is O-(omega-(9H-carbazole-9-yl)alkyl) hydroxylamine. The purifying method includes suspending the target product into water, adjusting the mixture to be acidic, extracting with an organic solvent to remove impurities, adjusting a water layer to be alkaline, extracting with an organic solvent, and recovering the organic solvent until the product is dry. The prepared product can be used for pre-column derivatization-liquid chromatography measurement of aldehydes or fluorescence labeling of aldehyde group containing compounds.

Description

technical field [0001] The invention belongs to the field of reagent synthesis and analysis and testing, and specifically relates to a method for preparing and purifying an O-substituted hydroxylamine fluorescence derivatization reagent. The purified reagent can be used for labeling and derivatization analysis and determination of aldehyde compounds or substances containing aldehyde groups . Background technique [0002] In recent years, aldehyde compounds have attracted people's attention. For example, formaldehyde in indoor air is one of the main pollutants, and long-term inhalation can easily lead to various diseases. Formaldehyde, acetaldehyde, propionaldehyde and other small molecule aldehydes can also be used as one of the indicators to identify waste oil. The absorption of these aldehydes into the body will lead to changes in the structure of proteins and DNA, leading to various diseases. [0003] Metabolism of substances in the body will also produce aldehyde compou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06G01N30/02G01N30/06
CPCC07D209/86C09K11/06C09K2211/1029G01N30/02G01N30/06
Inventor 肖莹王婉于清峰何华
Owner CHINA PHARM UNIV
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