Synthetic method of 4-hydroxyindole

A synthetic method, the technology of oxindole, which is applied in the field of synthesis of 4-oxindole, can solve the problems of high raw material cost, unfavorable industrial production, and harsh reaction conditions of 4-oxindole, and achieve convenient acquisition and reduced production cost , the effect of mild reaction conditions

Inactive Publication Date: 2021-03-26
ASTATECH CHENGDU BIOPHARM CORP
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that it requires high equipment, the operation is more complicated, and the cost is relatively high.
[0007] In summary, the methods for synthesizing 4-hydroxyindole in the prior art have problems such as high raw material cost, harsh reaction conditions, high equipment requirements, long reaction time and inconvenient post-processing, which lead to its unfavorable industrial production

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
  • Synthetic method of 4-hydroxyindole
  • Synthetic method of 4-hydroxyindole
  • Synthetic method of 4-hydroxyindole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthetic route of present embodiment is as follows:

[0041]

[0042] The method for preparing 4-oxindole in the present embodiment may further comprise the steps:

[0043] 1. Preparation of compound 2:

[0044]

[0045] Specific operation:

[0046](1) 1-chloro-2-methyl-3-nitrobenzene (100g, 1eq), BrettPhos PdG3 (0.53g, 0.001eq), Cs 2 CO 3 (379.78g, 2eq) and methanol (186.74g, 10eq) were added in 500mL toluene, and the reaction solution was 2 Under protection, the temperature was raised to 70°C for 16 hours.

[0047] (2) The remaining control raw material in the TLC plate is less than 5%, and a main point is generated.

[0048] (3) The reaction solution was lowered to room temperature, and added to 1 L of water. The aqueous phase was extracted with ethyl acetate (500 mL×3), and the organic phases were combined. The organic phase was washed with saturated brine (800ML×1), dried over anhydrous sodium sulfate, decolorized by adding 5g of activated carbon,...

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 belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of 4-hydroxyindole. Aiming at the problems existing in industrial production of 4-hydroxyindole in the prior art, the technical scheme of the invention is as follows: the method comprises the following steps: (1) protecting hydroxyl in a compound 3 by using a protective group to obtaina compound 4; (2) reacting the compound 4 with N, N-dimethylformamide dimethyl acetal to obtain a compound 5; (3) mixing the compound 5 with NH2NH2.H2O and MeOH, and carrying out a reaction to obtaina compound 6; and (4) removing the protective group of the compound 6 to obtain 4-hydroxyindole. According to the method for synthesizing 4-hydroxyindole, the cost of starting materials is low, the reaction conditions in the synthesis process are mild, operation is convenient, aftertreatment is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 4-hydroxyindole. Background technique [0002] Oxindole compounds are raw materials for the synthesis of many natural compounds, and the indole nucleus is often used as a prominent structural unit in many discovered natural products and pharmaceutically active compounds. Therefore, the development of new methods for the synthesis of indole core frameworks with different substitution patterns is an important goal of current organic synthesis. It is well known that many of these indole derivatives are synthetic pharmaceutical intermediates with physiological activity. [0003] 4-Hydroxyindole is an important organic chemical raw material and intermediate, which can be used to synthesize dyes, spices and some drugs, and can also be used as plant auxin and feed additive. 4-hydroxyindole is also an important intermediate for the synthesis ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08
CPCC07D209/08Y02P20/55
Inventor 庄明晨陶康谢坤山亢兴龙徐兴兵郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap