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Method for synthesizing 2,2'-biquinoline

A synthesis method and biquinoline technology are applied in 2 fields, can solve problems such as unfavorable industrial production, low product purity, expensive catalyst, etc., and achieve the effects of low cost, simple post-processing, and no reduction in yield

Inactive Publication Date: 2010-09-15
ZHEJIANG UNIV OF TECH
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  • 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

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  • 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 bottom flask, add H 2 O (5.0g), PEG-400 (1.0g), quinoline (1.0g), after stirring evenly, add 1% Pd / C catalyst (0.1g) and react at 80°C for 20h, cool the reaction solution and suction filter, The filter cake Pd / C was washed with water, which can be recycled and reused; the filtrate was extracted with ethyl acetate, the solvent was evaporated, concentrated, and crystals were precipitated to obtain a crude product, which was 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 bottom flask, add H 2 O (1.0g), PEG-1000 (2.0g), quinoline (1.0g), after stirring evenly, add 10% Pd / C catalyst (0.4g) and react at 140°C for 15h, cool the reaction solution and suction filter, The filter cake Pd / C was washed with water and could be recycled and reused; the filtrate was extracted with ethyl acetate, the solvent was evaporated, concentrated, and crystals were precipitated to obtain a crude product, which was recrystallized to obtain 0.53 g of white crystals, with a yield of 52.6%.

Embodiment 3

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

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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 present invention relates to a kind of synthetic method of 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 a metal complex of a conjugated system with a variety of 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 turn purple, and is a highly selective reagent for the determination of cuprous. Disodium 2,2'-biquinoline-4,4'-dicarboxylate is an excellent protein detection reagent. Biquinoline derivatives, as dopants for organic light-emitting devices, have important application values ​​in photoconduction, photoelectric conversion, photoelectrochemical catalysis, light sensitivity, gas sensitivity, etc., and show...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/12
CPCY02P20/584
Inventor 裴文董华
Owner ZHEJIANG UNIV OF TECH
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