Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of 4-chloroindole-3-acetic acid

A technology of chloroindole and acetic acid, which is applied in the field of preparation of 4-chloroindole-3-acetic acid, can solve the problems of low total yield, incapable of large-scale production, high cost and the like, and achieves low price, safe preparation process without any problems. dangerous effect

Active Publication Date: 2018-04-06
SUZHOU CANIMBLE BIOTECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] People such as Hiroyuki Ishibashi (J.CHEM.SOC.PERKIN TRANS.1992) have reported the synthesis of analogue, have adopted following route, and this route reaction step is longer, and total yield is lower than 40%, has adopted a non-marketable Sulfur-containing raw materials are expensive, and the post-reaction treatment is cumbersome and cannot be produced on a large scale

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
  • A kind of preparation method of 4-chloroindole-3-acetic acid
  • A kind of preparation method of 4-chloroindole-3-acetic acid
  • A kind of preparation method of 4-chloroindole-3-acetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A preparation method of 4-chloroindole-3-acetic acid, the steps are as follows:

[0039] 1) Synthesis of N,N-dimethyl-2-chloro-6-nitrostyrylamine: 200g of 2-chloro-6-nitrotoluene and 183g of DMFDMA were added to 150ml of anhydrous DMF solution, heated To 80 ~ 120 ℃, heat preservation reaction for 4 hours, use GC detector to detect the reaction end point, after the reaction is complete, cool the obtained product to room temperature, and add 1L toluene solution to the reaction system to dissolve the product, after dissolution, use saturated salt Wash with water, then dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 290 g of crude N,N-dimethyl-2-chloro-6-nitrostyrylamine;

[0040] 2) Synthesis of 4-chloroindole: 290g of crude N,N-dimethyl-2-chloro-6-nitrostyrylamine was dissolved in a mixed solvent of 250mlTHF and 250ml methanol, and after dissolution, the , At 30°C, add 40g of Raney nickel, and dropwise add 300ml of hydrazine hy...

Embodiment 2

[0061] A preparation method of 4-chloroindole-3-acetic acid, the steps are as follows:

[0062] 1) Synthesis of N,N-dimethyl-2-chloro-6-nitrostyrylamine: same as Example 1.

[0063] 2) Synthesis of ethyl 4-chloroindole-3-acetate: 290 g of N,N-dimethyl-2-chloro-6-nitrostyrylamine crude product prepared in step 1) was dissolved in 500 ml of methanol solvent After dissolving, add 40g of Raney nickel and dropwise add 300ml of hydrazine hydrate with a concentration of 80% under nitrogen protection at 15°C to make N,N-dimethyl-2-chloro-6-nitro -NO in styrylamine 2 Reduction to -NH 2 , The C-N bond in -C=C-N- in N,N-dimethyl-2-chloro-6-nitrostyrylamine is broken, and the ring closure reaction is carried out in the reaction system, the obtained product is filtered, the filtrate is concentrated, Distillation under reduced pressure gave 112 g of pure 4-chloroindole, and the combined steps 1) and 2) were used to calculate the yield. The molar yield of 4-chloroindole was 63.5%, and its...

Embodiment 3

[0067] A preparation method of 4-chloroindole-3-acetic acid, the steps are as follows:

[0068] 1) Synthesis of N,N-dimethyl-2-chloro-6-nitrostyrylamine: same as Example 1.

[0069] 2) Synthesis of 4-chloroindole-3-ethyl acetate: same as Example 1.

[0070] 3) Synthesis of 4-chloroindole-3-ethyl acetate: same as Example 1.

[0071] 4) Synthesis of 4-chloroindole-3-acetic acid: the 4-chloroindole-3-ethyl acetate crude product of 130g is dissolved in the mixed solvent of 500ml water and 500ml methyl alcohol, adds the sodium hydroxide of 120g, is heated to Reflux at 60-70°C for 3 hours. Then the reaction solution was concentrated to dryness under reduced pressure, the residue was dissolved in 500ml of water, 500ml of dichloromethane was added for washing and layering, the pH of the aqueous phase was adjusted to 1-2 with concentrated hydrochloric acid, and then extracted with ethyl acetate, Merge with the organic phase, then dry over anhydrous sodium sulfate, concentrate to obt...

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 4-chloroindole-3-acetic acid preparing method. The method specifically comprises the steps of 1, conducting condensation reaction of a compound i and DMFDMA at the temperature of 80-120 DEG C in anhydrous DMF solvent, so that a compound ii is generated; 2, dissolving the compound ii in solvent formed by mixing THF with alcohol, adding Raney nickel and adding hydrazine hydrate dropwise for reaction at the temperature of 15-30 DEG C in an inert atmosphere, and obtaining a compound iii after reaction ends completely; 3, dissolving the compound iii in solvent, adding inorganic strong base and a phase transfer catalyst, adding a compound iv dropwise at the temperature of 20-35 DEG C for substitution reaction, conducting heating for backflow after the compound iv is added, and obtaining a compound v after reaction ends completely; 4, hydrolyzing the compound v to obtain the target product 4-chloroindole-3-acetic acid. According to the preparing method, no highly-toxic product is adopted as raw materials, and the whole reaction process is safe.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 4-chloroindole-3-acetic acid. Background technique [0002] 4-chloroindole-3-acetic acid (4-CIAA), is a kind of IAA (indole acetic acid) plant growth hormone, which can not only promote growth, but also inhibit growth; both can accelerate germination, and can also inhibit germination; It can prevent flowers and fruits from falling, and it can also thin flowers and fruits, which has duality. [0003] The synthetic method of existing 4-chloroindole-3-acetic acid has the following several kinds: [0004] Masato et al. (Biosci.Biotechnol.Biochem.,64(4),808-815,2000) synthesized 4-chloroindole-3-acetic acid and its related ester compounds, the method has a long route, the total yield of the three-step reaction is 58.9%, the product purity is low, and a highly toxic cyanide is used simultaneously, which is not conducive to the industrial production of the prod...

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 Patents(China)
IPC IPC(8): C07D209/18
CPCC07D209/18
Inventor 曾鹏程顾晓春刘宁陆超
Owner SUZHOU CANIMBLE BIOTECH
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com