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

Method for synthesizing 2,2'-biquinoline

A synthetic method, the technology of biquinoline, applied in 2 fields, can solve the problems of unfavorable industrial production, expensive catalysts, high cost of raw materials, etc., and achieve the effects of low cost, no reduction in yield, high product yield and purity

Inactive Publication Date: 2008-03-05
ZHEJIANG UNIV OF TECH
View PDF0 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has high raw material cost and low product purity, which is not conducive to industrial production
[0004] The above method of synthesizing 2,2'-biquinoline, or raw material cost is too high, or uses expensive catalyst

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
  • Method for synthesizing 2,2'-biquinoline
  • Method for synthesizing 2,2'-biquinoline
  • Method for synthesizing 2,2'-biquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 50 mL round-bottomed flask, H was added sequentially 2 O (5.0g), PEG-400 (1.0g), quinoline (1.0g), after stirring evenly, 1% Pd / C catalyst (0.1g) was added to react at 80°C for 20h, the reaction solution was cooled and suction filtered, The filter cake Pd / C is washed with water, and can be recovered and reused; the filtrate is extracted with ethyl acetate, the solvent is evaporated, concentrated, and crystals are separated out to obtain a crude product, which is recrystallized to obtain 0.12 g of white 2,2'-biquinoline crystals, The yield is 11.9%, and the melting point is 196-197°C. 1 H NMR (400MHz, CDCl 3 ) δppm: 8.86 (d, 2H, J=8.1Hz), 8.34 (d, 2H, J=8.6Hz), 8.25 (dd, 2H, J=2.4Hz), 7.89 (dd, 2H, J=7.0Hz) , 7.59 (m, 2H), 7.77 (m, 2H); 13 C NMR (CDCl 3 ) δppm: 152, 147.5, 137, 129.5, 128.0, 127.5, 127.0, 119.0; MS (EI): m / z (%): 256 (100) [M + ], 128(30), 101(13).

Embodiment 2

[0028] In a 50 mL round-bottomed flask, H was added sequentially 2 O (1.0g), PEG-1000 (2.0g), quinoline (1.0g), after stirring evenly, 10% Pd / C catalyst (0.4g) was added to react at 140°C for 15h, the reaction solution was cooled and suction filtered, The filter cake Pd / C is washed with water and can be recovered and reused; the filtrate is extracted with ethyl acetate, the solvent is evaporated, concentrated, and crystals are precipitated to obtain a crude product, which is recrystallized to obtain 0.53 g of white crystals, the yield is 52.6%.

Embodiment 3

[0030] In a 50 mL round-bottomed flask, H was added sequentially 2 O (3.0g), PEG-400 (3.0g), quinoline (1.0g), after stirring evenly, 5% Pd / C catalyst (1.0g) was added to react at 120°C for 4h, the reaction solution was cooled and suction filtered, The filter cake Pd / C is washed with water and can be recovered and reused; the filtrate is extracted with ethyl acetate, the solvent is evaporated, concentrated, and crystals are precipitated to obtain a crude product, which is recrystallized to obtain 0.58 g of white crystals, the yield is 57.6%.

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 present invention relates to 2, 2'-biquinoline synthesizing process. Inside water and polyethylene glycol (PEG) solvent system and in the presence of Pd / C catalyst, quinoline material is reacted at 140 deg.c for 4-20 hr to obtain 2, 2'-biquinoline. In the reaction system, the weight ratio between PEG and water is 0.2-2 to 1, the Pd / C catalyst has Pd supporting amount of 1-10 wt%, the PEG has molecular weight of 400-6000, the weight ratio between the Pd / C catalyst and quinoline is 0.1-1 to 1, and the weight ratio between the water / PED solvent system and quinoline is 3-10 to 1. The present invention has low material cost, simple operation, high yield and less environmental pollution, and is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 2,2'-biquinoline. (2) Background technology [0002] As important organic raw materials, 2,2'-biquinoline and its derivatives are widely used in medicine, detection, optoelectronic materials and other fields. Biquinoline can form metal complexes of conjugated systems with various metals, and has a wide range of applications in the detection and content determination of trace metals. For example, 2,2'-biquinoline, also known as cuprous reagent, reacts with monovalent cupric ions to give a purple color, and is a highly selective reagent for the determination of cuprous. Disodium 2,2'-biquinoline-4,4'-dicarboxylate is an excellent protein detection reagent. Derivatives of biquinoline, as dopants of organic light-emitting devices, have important application value in photoconductivity, photoelectric conversion, photoelectrochemical catalysis, photosensitivity, gas sensing, etc., showing good applicati...

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): C07D215/12
CPCY02P20/584
Inventor 裴文董华
Owner ZHEJIANG UNIV OF TECH
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