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

Preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol

A quinolinyl and propyne technology is applied in the field of preparation of 3--2-propyn-1-ol, can solve problems such as non-compliance with environmental protection requirements, unfriendly environment, etc., and achieves cost reduction, reaction yield improvement, The effect of reducing harm to the environment

Inactive Publication Date: 2012-11-07
SHANGHAI INST OF PHARMA IND
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the above method (document US2003199696A1), the Sonogashira reaction of 3-bromoquinoline and propargyl alcohol needs to use the organic solvent triethylamine as a solvent, which is not environmentally friendly and does not meet environmental protection requirements

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 3-(3-quinolyl)-2-propyne-1-alcohol
  • Preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of 3-(3-quinolyl)-2-propyn-1-alcohol:

[0021] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.04g cuprous iodide, 0.07g bis(triphenylphosphine) palladium dichloride (Pd(PPh 3 ) 2 Cl 2 ), 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, and the reaction of raw materials is complete after 40min. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.74 g (98.8%) of solid.

Embodiment 2

[0023] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.4g cuprous iodide, 0.7gPd(PPh 3 ) 2 Cl 2 , 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, 40min after the reaction of raw materials is complete. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.75 g (99.4%) of solid.

Embodiment 3

[0025] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.08g cuprous iodide, 0.07gPd(PPh 3 ) 2 Cl 2 , 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, 40min after the reaction of raw materials is complete. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.73 g (98.3%) of solid.

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 the technical field of a preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol. According to the preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol, tribromoquinoline reacts with propargyl alcohol in water in the presence of alkali and under the catalysis of palladium and cuprous iodide. According to the invention, water is used as a solvent, and a compound as shown in the formula (II) is prepared by the reaction between a compound as shown in the formula (I) and propargyl alcohol at normal temperature or at the temperature of 15-100 DEG C in the presence of alkali and under the catalysis of palladium and cuprous iodide. By the method, water can be used as a solvent. Therefore, the harm to the environment is minimized, cost is relatively reduced, and reaction yield is also raised.

Description

technical field [0001] The present invention relates to the preparation method of 3-(3-quinolyl)-2-propyn-1-alcohol, specifically, it relates to the reaction of 3-bromoquinoline and propargyl alcohol to prepare 3-(3-quinolyl) - The technical field of the method of 2-propyn-1-ol. Background technique [0002] Preparation of 3-(3-quinolyl)-2-propyn-1-alcohol generally takes 3-bromoquinoline as raw material, which can be prepared by the following method: [0003] 3-bromoquinoline (I) first reacts with propargyl alcohol to obtain formula (II) compound by Sonogashira [0004] [0005] In the above method (document US2003199696A1), the Sonogashira reaction between 3-bromoquinoline and propargyl alcohol requires the use of organic solvent triethylamine as a solvent, which is not environmentally friendly and does not meet environmental protection requirements. Contents of the invention [0006] The purpose of the present invention is to solve the above problems, reduce enviro...

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): C07D215/14
Inventor 毕万福陈旭东单晓燕时惠麟
Owner SHANGHAI INST OF PHARMA IND
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