3-methylpyrazolyl benzaldehyde 4-aminoantipyrine Schiff base and preparation method thereof

A technology of aminoantipyrine and methylpyrazolyl, applied in the field of 3-methylpyrazolylbenzaldehyde acetal 4-aminoantipyrine Schiff base and its preparation, to achieve good specific selectivity, fast Response to the effect of pH adaptation range

Active Publication Date: 2018-09-07
徐州世威隆盛建设工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although researchers have carried out many reactions using pyrazole, there are no relevant reports on the synthesis of 3-methylpyrazole and 4-aminoantipyrine as raw materials and their use as fluorescent probes for metal ion detection.

Method used

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  • 3-methylpyrazolyl benzaldehyde 4-aminoantipyrine Schiff base and preparation method thereof
  • 3-methylpyrazolyl benzaldehyde 4-aminoantipyrine Schiff base and preparation method thereof
  • 3-methylpyrazolyl benzaldehyde 4-aminoantipyrine Schiff base and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Weigh 0.82g (10mmol) of 3-methylpyrazole and 2.32g (16.8mmol) of potassium carbonate, dissolve them in 20mL of N,N-dimethylformamide, and add them to a 100mL tetrachloride equipped with a thermometer and a stirring device. mouth flask. React under constant temperature stirring at 100°C, add 1.24g (10mmol) of p-fluorobenzaldehyde to the mixed solution, continue the reaction for 16h, cool to room temperature, filter, extract, separate by column chromatography, concentrate under reduced pressure, wash with warm water, and reconstitute with ether Crystallize and dry in vacuum at 50°C for 8 hours to obtain 3-methylpyrazolylbenzaldehyde.

[0031] Weigh 0.93g (5mmol) of 3-methylpyrazolylbenzaldehyde and 1.01g (5mmol) of 4-aminoantipyrine, dissolve them in 4mL of N,N-dimethylformamide, and add them to a thermometer equipped with a thermometer. , A 10mL single-necked flask with a stirring device. Add 0.12 g (2 mmol) of glacial acetic acid to the above mixed solution, react at ...

Embodiment 2

[0033] Weigh 0.82g (10mmol) of 3-methylpyrazole and 2.32g (16.8mmol) of potassium carbonate, dissolve them in 15mL of N,N-dimethylformamide, and add them to a 100mL tetrachloride equipped with a thermometer and a stirring device. mouth flask. React under constant temperature stirring at 110°C, add 3.1 g (25 mmol) of p-fluorobenzaldehyde to the mixed solution, continue the reaction for 16 h, cool to room temperature, filter, extract, separate by column chromatography, concentrate under reduced pressure, wash with warm water, and reconstitute with ether Crystallize and dry in vacuum at 50°C for 8 hours to obtain 3-methylpyrazolylbenzaldehyde.

[0034] Weigh 0.186g (1mmol) of 3-methylpyrazolylbenzaldehyde and 0.202g (1mmol) of 4-aminoantipyrine, dissolve them in 5mL of N,N-dimethylformamide, and add to the , A 10mL single-necked flask with a stirring device. Add 0.30 g (5 mmol) of glacial acetic acid to the above mixed solution, react at 85 °C for 4 h under constant temperature...

Embodiment 3

[0036] Weigh 1.64g (20mmol) of 3-methylpyrazole and 5.53g (40mmol) of potassium carbonate, dissolve them in 30mL of N,N-dimethylformamide, and add them to a 100mL four-port tube equipped with a thermometer and a stirring device. in the flask. React under constant temperature stirring at 120°C, add 1.61 g (13 mmol) of p-fluorobenzaldehyde to the mixed solution, continue the reaction for 18 h, cool to room temperature, filter, extract, separate by column chromatography, concentrate under reduced pressure, wash with warm water, and reconstitute with ether Crystallize and dry in vacuum at 50°C for 8 hours to obtain 3-methylpyrazolylbenzaldehyde.

[0037]Weigh 0.186g (1mmol) of 3-methylpyrazolylbenzaldehyde and 1.01g (0.5mmol) of 4-aminoantipyrine, dissolve them in 4mL of N,N-dimethylformamide, add to the In a 10mL single-necked flask with a thermometer and a stirring device. Add 0.12 g (2 mmol) of glacial acetic acid to the above mixed solution, react at 80 °C for 4 h under cons...

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Abstract

The invention discloses a Schiff base fluorescent probe and use thereof in detecting lead ions, relates to a fluorescent probe which is markedly enhanced in fluorescence in the presence of the lead ions, and provides a 3-methylpyrazolyl benzaldehyde 4-aminoantipyrine Schiff base for selectively detecting the lead ions and a preparation method thereof. Firstly, 3-methylpyrazole and p-fluorobenzaldehyde are used as raw materials to prepare 3-methylpyrazole benzaldehyde, and a Schiff base with a larger conjugated PI structure is obtained by condensation reaction of an aldehyde group and a primaryamine of the 3-methylpyrazolyl benzaldehyde and 4-aminoantipyrine. The process has the advantages of easy availability of raw materials, low synthesis cost, simple operation, easy preparation, high yield and the like. The probe has good selectivity to the lead ions, easy identification, fast response time and strong pH adaptability and other characteristics, is a simple and sensitive specific detection reagent that can quickly identify the lead ions, can be used in the field of materials or sensors, and has potential application value in the field of biological environment testing.

Description

technical field [0001] The invention relates to a 3-methylpyrazolylbenzaldehyde acetal 4-aminoantipyrine Schiff base and a preparation method thereof. The compound has a conjugated and rigid planar structure, exhibits good fluorescence performance, and contains The C=N functional group can provide abundant coordination modes and has a strong metal coordination ability, thus having good metal ion selectivity. Background technique [0002] Pyrazole is a heterocyclic compound containing two nitrogen atoms. As a very important organic synthesis intermediate, it is mainly used in the fields of halogen-containing solvents, lubricating oil stabilizers, chelating agents, and organic synthesis intermediates. The nitrogen atom on the ring, due to the lone pair of electrons, enables it to coordinate and adsorb with various metal ions (such as lead ions and chromium ions (Ⅲ), etc.), and can form a variety of single-dentate, multi-dentate, etc. Ligand structure, so pyrazole plays an inc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/38C09K11/06G01N21/64
CPCC07D231/38C09K11/06C09K2211/1044G01N21/6428
Inventor 房士敏孟霞段洪东杨耿
Owner 徐州世威隆盛建设工程有限公司
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