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

Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof

A technology of oxindoline and hydrohalide, which is applied in the field of compound 5, can solve problems such as being unsuitable for industrial production, and achieve the effects of good stability, less side reactions, and high reaction yield

Active Publication Date: 2018-01-05
烟台六谛医药科技有限公司
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The present invention aims at the deficiency that the existing disclosed 5,6-dihydroxyindoline and its hydrohalide salt preparation method cannot be applied to industrial production, and provides a compound 5,6-dihydroxyindoline and its hydrogen halide Preparation method of acid salt

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
  • Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
  • Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
  • Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] A kind of preparation method of 5,6-dihydroxyindoline, comprises the steps:

[0050] 1) Synthesize amide SM-1 with 3,4-dimethoxyethylamine and acetyl chloride as raw materials, the chemical equation is:

[0051]

[0052] The specific operation process is as follows: install mechanical stirring, constant pressure dropping funnel and built-in thermometer on a 1L three-neck round bottom flask; the outside is ethanol circulating cooling liquid. 90.56g (0.5mol) of 3,4-dimethoxyphenethylamine, 100mL (0.72mol) of triethylamine and 455mL of dichloromethane were sequentially added into the reaction flask. Under the condition of stirring, the above mixed solution was lowered to 0°C. Then, measure 0.60 mol of acetyl chloride or acetic anhydride, and transfer it to a constant pressure dropping funnel; at an internal temperature of 0°C, drop acetyl chloride or acetic anhydride into the above reaction solution; the dropping time lasts about 20-30 minutes . After the dropwise ad...

Embodiment 2

[0070] A kind of preparation method of 5,6-dihydroxyindoline hydrobromide, comprises the steps:

[0071] 1) Synthesize amide SM-1 with 3,4-dimethoxyethylamine and acetyl chloride as raw materials, the chemical equation is:

[0072]

[0073] The specific operation process is as follows: install mechanical stirring, constant pressure dropping funnel and built-in thermometer on a 1L three-neck round bottom flask; the outside is ethanol circulating cooling liquid. 90.56g (0.5mol) of 3,4-dimethoxyphenethylamine, 100mL (0.72mol) of triethylamine and 455mL of dichloromethane were sequentially added into the reaction flask. Under the condition of stirring, the above mixed solution was lowered to -5°C. Then, measure 0.60 mol of acetyl chloride or acetic anhydride, and transfer it to a constant pressure dropping funnel; at an internal temperature of 0°C, drop acetyl chloride or acetic anhydride into the above reaction solution; the dropping time lasts about 20-30 minutes . After t...

Embodiment 3

[0088] A kind of preparation method of 5,6-dihydroxyindoline, comprises the steps:

[0089] 1) Using 3,4-dimethoxyethylamine and tert-valeryl chloride as raw materials to synthesize amide SM-1, the chemical equation is:

[0090]

[0091] The specific operation process is as follows: install mechanical stirring, constant pressure dropping funnel and built-in thermometer on a 1L three-neck round bottom flask; the outside is ethanol circulating cooling liquid. 90.56g (0.5mol) of 3,4-dimethoxyphenethylamine, 100mL (0.72mol) of triethylamine and 455mL of dichloromethane were sequentially added into the reaction flask. Under the condition of stirring, the above mixed solution was lowered to 0°C. Then, measure 0.6 mol of t-valeryl chloride and transfer it to a constant pressure dropping funnel; add t-valeryl chloride dropwise to the above reaction solution at an internal temperature of 0°C; the dropping time lasts about 20-30 minutes. After the dropwise addition, react at 0° C. ...

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 relates to a preparation method of a compound 5,6-dihydroxy indoline and halogen acid salts thereof. Phenylethylamine SM-0 sold in the market is used as a raw material and firstly reactswith acyl chloride to obtain amide SM-1; amide SM-1 reacts with halogen to obtain a compound as shown in the formula III; the compound as shown in the formula III undergoes intramolecular cyclizationunder the catalysis of copper oxalate to generate a compound as shown in the formula IV; and the compound as shown in the formula IV reacts with halogen acids to respectively obtain the expected target compounds as shown in the formula I and formula II. The invention has the following beneficial effects: 1) cheap copper oxalate is used as a catalyst of the cyclization, raw materials are cheap andeasily available, and the method for preparing the compound as shown in the formula IV from the compound as shown in the formula III has advantages of high reaction yield and less side reaction and is suitable for industrial production; and 2) the whole process is simple to operate, and the products obtained have high purity and good stability and are easy to store and use for a long time.

Description

technical field [0001] The invention relates to a preparation method of a compound 5,6-dihydroxyindoline and a hydrohalide salt thereof, belonging to the technical field of organic synthesis. Background technique [0002] 5,6-dihydroxyindoline, also known as 5,6-dihydroxyindoline, English name Indoline-5,6-diol or 2,3-dihydro-1H-indole-5,6-diol, CAS Number: 29539-03-5, with formula I structural formula: [0003] [0004] The hydrohalic acid (HX) salt of 5,6-dihydroxyindoline has the structural formula shown in formula II, specifically including two forms of expression a and b: [0005] [0006] Among them, hydrohalic acid HX mainly refers to hydrochloric acid, hydrobromic acid, etc.; formula II-a refers to the general structural formula of hydrohalide salt of 5,6-dihydroxyindoline, and formula II-b refers to 5,6-dihydroxyindoline Oxindoline hydrohalide actually exists in the form of positive and negative ion pairs. [0007] 5,6-Dihydroxyindoline is an important inte...

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): C07D209/08
Inventor 杨家德曲文超王秀杰范玉龙陈婷婷
Owner 烟台六谛医药科技有限公司
Features
  • Generate Ideas
  • 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