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Preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone

A technology of 3-c, pyrazolone, applied in directions such as organic chemistry, can solve problems such as no reports, and achieve the effects of convenient post-processing, high yield, and simple synthesis process

Inactive Publication Date: 2018-08-14
SOUTHWEST PETROLEUM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, spiro[chromenoyl (2,3 -c) The method of pyrazole-4,1-isobenzofuran]-3-one, there is no report at present

Method used

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  • Preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone
  • Preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone
  • Preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Starting materials: 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid; 1-phenyl-3-methyl-5-pyrazolone; concentrated sulfuric acid.

[0037] In 5 mL of concentrated sulfuric acid, add 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid and 1-phenyl-3-methyl-5-pyrazolone in molar ratio, The reaction was heated to reflux at 90°C for 5 hours.

[0038] Separation and purification: After the reaction solution is cooled to room temperature, slowly add an appropriate amount of ice water, and the precipitation is complete. After suction filtration, wash with a large amount of water to obtain a red solid crude product, which is further purified with a silica gel column. The developer is ethyl acetate: petroleum ether =(1:5~1:3) gradient elution, the orange-red color band was collected, and after rotary evaporation, a white and reddish powder was obtained.

[0039] Yield 73%. Chemical formula C 32 h 33 N 3 o 3 , the proton nuclear magnetic spectrum, carbon nuclear magnetic spe...

Embodiment 2

[0043] Starting materials: 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid; 1-H-3-methyl-5-pyrazolone; concentrated sulfuric acid.

[0044] In 5 mL of concentrated sulfuric acid, add 1 mmol of 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid and 1-H-3-methyl-5-pyrazolone to make The reaction was heated to reflux at 90°C for 5 hours.

[0045] Separation and purification: After the reaction solution is cooled to room temperature, slowly add an appropriate amount of ice water, and the precipitation is complete. After suction filtration, wash with a large amount of water to obtain a red solid crude product, which is further purified with a silica gel column. The developer is ethyl acetate: petroleum ether =(1:5~1:3) gradient elution, the orange-red color band was collected, and after rotary evaporation, a white solid powder was obtained.

[0046] Yield 52%. Chemical formula C 26 h 29 N 3 o 3 , the proton nuclear magnetic spectrum, carbon nuclear magnetic spectrum, high re...

Embodiment 3

[0050] Starting materials: 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid; 1-(4-chlorophenyl)-3-methyl-5-pyrazolone; concentrated sulfuric acid.

[0051] In 5 mL of concentrated sulfuric acid, add 1 mmol of 2-(4-(dibutylamino)-2-hydroxybenzoyl)benzoic acid and 1-(4-chlorophenyl)-3-methyl-5- Pyrazolone, the reaction was heated to reflux at 90°C for 5 hours.

[0052] Separation and purification: After the reaction liquid is cooled to room temperature, slowly add an appropriate amount of ice water, and the precipitation is complete. After suction filtration, wash with a large amount of water to obtain a red solid crude product, which is further purified with a silica gel column. The developer is ethyl acetate: petroleum ether =(1:5~1:3) gradient elution, the orange-red color band was collected, and after rotary evaporation, a pale pink solid powder was obtained.

[0053] Yield 68%. Chemical formula C 32 h 32 ClN 3 o 3 , the proton nuclear magnetic spectrum, carbon nuclea...

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone. The preparation method comprises the stepsof in concentrated sulfuric acid, adding 2-(4-(dibutylamine)-2-hydroxybenzoyl)benzoic acid and 1-pyrazolone, reacting at 90 DEG C for 5 hours, separating and purifying through a silica gel chromatography column to obtain a product. The preparation method of spiro[chromene(2,3-c)pyrazole-4,1'-isobenzofuran]-3-ketone provided by the invention is convenient in synthesis operation, and chemical technologies used in the whole experiment process are the most common experiment operations.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of spiro[chromeno(2,3-c)pyrazole-4,1′-isobenzofuran]-3-one. Background technique [0002] Spiro[chromeno(2,3-c)pyrazole-4,1′-isobenzofuran]-3-one is a kind of artificially synthesized lactone compounds. It has a wide range of application values ​​in the fields of fluorescent probes and dyes. Therefore, chemical modification of spiro[chromeno(2,3-c)pyrazole-4,1′-isobenzofuran]-3-one to synthesize derivatives with various reactive groups provides platform. [0003] Under certain conditions, when the ions or molecules in the solution coordinate with the rhodamine lactone ring, it will also lead to the opening of the lactone ring, resulting in changes in color and fluorescence. The ring-opening of the spiro derivatives and the detected substance to generate a fluorescent response has become the guiding idea for the construction of this type of probe molecule. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/20
CPCC07D491/20
Inventor 解正峰郝云鹏石伟包万睿王馨任兴栋张杰刘侨
Owner SOUTHWEST PETROLEUM UNIV