Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

1-(4-isopropylbenzene-yl)-3-methyl-5-pyrazolone, preparation method and application thereof

A technology of cumylphenyl and pyrazolone, applied in the field of organic chemical synthesis, can solve the problems of cumbersome removal of excess reagents, few types of separated monosaccharides, high polarity, etc., and achieve mild conditions, less environmental pollution, and simple operation Effect

Inactive Publication Date: 2010-08-18
NORTHWEST UNIV
View PDF1 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the PMP reagent itself also has disadvantages such as high polarity, cumbersome removal of excess reagent, and few types of monosaccharides to be separated.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 1-(4-isopropylbenzene-yl)-3-methyl-5-pyrazolone, preparation method and application thereof
  • 1-(4-isopropylbenzene-yl)-3-methyl-5-pyrazolone, preparation method and application thereof
  • 1-(4-isopropylbenzene-yl)-3-methyl-5-pyrazolone, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the synthesis of 1-phenyl-3-methyl-5-pyrazolone

[0019] Weigh 2.160 g (0.02 mol) of phenylhydrazine, add 2.5 mL of ethyl acetoacetate and 2.5 mL of glacial acetic acid dropwise, and react with magnetic stirring for about 4 hours at room temperature, and detect the end point of the reaction by TLC. The glacial acetic acid was evaporated in vacuum, the product was dissolved in methanol, recrystallized, filtered, and the filter cake was air-dried to constant weight to obtain 2.701 g of off-white powder 1-phenyl-3-methyl-5-pyrazolone (PMP) , and the yield was 77.58%.

Embodiment 2

[0020] Embodiment 2: Synthesis of 1-(4-isopropylphenyl)-3-methyl-5-pyrazolone

[0021] Weigh 3.734 g (0.02 mol) of 4-isopropylphenylhydrazine hydrochloride, add dropwise 17 mL of 5% NaOH solution for neutralization, and at room temperature, stir and react for 4 h, then neutralize with 1 mol / L hydrochloric acid to pH= 8-9, then use CH 2 Cl 2 After extraction and evaporation to dryness, 2.90 g (0.0192 mol) of light yellow solid 4-isopropylphenylhydrazine was obtained, with a yield of 96.76%.

[0022] To the solid 4-isopropylphenylhydrazine obtained above, 2.5 mL of ethyl acetoacetate and 2.9 mL of glacial acetic acid were added dropwise, and the reaction was carried out under magnetic stirring for about 4 hours at room temperature, and the end point of the reaction was detected by TLC. The glacial acetic acid was evaporated in vacuo, the product was passed through a silica gel column, and eluted with petroleum ether: ethyl acetate = 4:1; collected by TLC, and a small amount of...

Embodiment 3

[0023] Embodiment 3: Synthesis of 1,3-diphenyl-5-pyrazolone

[0024] Weigh 2.160g (0.02mol) of phenylhydrazine, add 3.46mL of ethyl benzoylacetate and 2.5mL of glacial acetic acid dropwise, and grind and stir at room temperature for about 3 hours to generate a large amount of white milky solid. The end point of the reaction is detected by TLC. The solid product was washed with a small amount of n-hexane, recrystallized with methanol-ethanol, filtered, and the filter cake was naturally dried to constant weight to obtain 4.418 g of milky white powder 1,3-diphenyl-5-pyrazolone (DPP for short). The yield was 93.6%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing 1-(4-isopropylbenzene-yl)-3-methyl-5-pyrazolone by catalysis at low temperature without a solvent. The method comprises the steps of: mixing 4-isopropyl phenyl hydrazine and ethyl acetoacetate which are used as raw materials and glacial acetic acid used as a catalyst and reacting at room temperature without adding any reaction solvents; and moreover, the yield obtained by the method can be more than 73%. The compound can be used for reducing sugar mark. The synthesis method has the advantages of less environmental pollution, high reaction yield and simple operation and can be used for scale production of the target product.

Description

technical field [0001] The invention relates to a synthesis method of 1-(4-isopropylphenyl)-3-methyl-5-pyrazolone and its application in reducing sugar labeling, belonging to the technical field of organic chemical synthesis. Background technique [0002] 1-Phenyl-3-methyl-5-pyrazolone (PMP for short) is a commonly used labeling reagent for carbohydrates. The labeling of this reagent and carbohydrates is mainly based on the pyrazolone under alkaline conditions The active methylene group on the ring undergoes a condensation reaction with the reducing end of the sugar, so that the sugar chain carries a pyrazolone derivative. The labeling reaction conditions are mild. Compared with the widely used reductive amination reagents for labeling sugars under acidic conditions, it will not cause the loss of acid-sensitive active groups on sugar chains, and is suitable for various types of sugar chains. mark. However, the PMP reagent itself also has disadvantages such as high polarity...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D231/26G01N30/00
Inventor 黄琳娟张萍解明明王仲孚
Owner NORTHWEST UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com