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Preparation method of 2-chloro-3-formyl quinoline derivatives

A technology of formyl quinolines and derivatives, which is applied in the field of preparation of quinoline derivatives, can solve problems such as transportation and storage hazards, pollute the environment, and corrode equipment, and achieve low cost, safe reaction process, and low environmental pollution Effect

Active Publication Date: 2017-06-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These halogenated reagents are toxic and corrosive and absorb moisture when exposed to air
Phosphorus trichloride and thionyl chloride will also produce a series of waste liquid and waste gas such as phosphoric acid and sulfur dioxide during use, which will corrode equipment and pollute the environment
Phosgene is a good halogenation reagent, and the product prepared with phosgene has high content and high yield, but phosgene is a highly toxic gas, which is very dangerous during use, transportation and storage

Method used

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  • Preparation method of 2-chloro-3-formyl quinoline derivatives
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Examples

Experimental program
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Effect test

Embodiment 1

[0023] The present embodiment provides the synthetic method of 2-chloro-3-formyl quinoline, and its main steps are as follows:

[0024] Under an ice-salt bath, stir and mix 2.73g (20.22mmol) of acetanilide, 8.19g (27.58mmol) of BTC and 10mL of chloroform. When the temperature is kept below -5°C, add 4.2mL (54.66mmol) dropwise within 30min DMF, the drop rate is controlled by the bubble overflow rate of the tail gas absorption device; after all the DMF is added dropwise, continue to stir in the ice salt bath for 10 minutes, change the water bath, heat to 40 ° C, react for 4 hours, evaporate part of the solvent, add ice water, 10 Adjust the pH to 8-9 with % NaOH, filter with suction, recrystallize from ethyl acetate, and the yield is 91.62%. Melting point: 157~159℃, m / Z:192.04[M+H] + .

Embodiment 2

[0029] The present embodiment provides the synthetic method of 2-chloro-3-formyl quinoline, and its main steps are as follows:

[0030] Under an ice-salt bath, stir and mix 2.73g (20.22mmol) of acetanilide, 4.17g (14.04mmol) of BTC and 10mL of chloroform. When the temperature is kept below -5°C, add 4.2mL (54.66mmol) dropwise within 30min DMF, the drop rate is controlled by the bubble overflow rate of the tail gas absorption device. After all the DMF was added dropwise, continue to stir in the ice-salt bath for 10 minutes, change the water bath, heat to 41°C, monitor the reaction progress by TLC, react for 4 hours, evaporate part of the solvent, quench with ice water, adjust the pH to 8 with 10% NaOH ~9, suction filtration, recrystallization from ethyl acetate, yield 75.92%.

Embodiment 3

[0032] The present embodiment provides the synthetic method of 2-chloro-3-formyl quinoline, and its main steps are as follows:

[0033] Under ice-salt bath, 2.73g (20.22mmol) of acetanilide and 4.2mL (54.66mmol) of DMF were stirred and mixed. When the temperature was kept below -5°C, 10mL of 8.03g (27.04mmol) of BTC was added dropwise within 50min. Chloroform solution, the drop rate is controlled by the bubble overflow rate of the tail gas absorption device. After all the drops were completed, continue to stir in the ice-salt bath for 10 minutes, change the water bath, heat to 45°C, monitor the reaction progress by TLC, react for 4 hours, evaporate part of the solvent, quench with ice water, and adjust the pH to 8-8 with 10% NaOH 9. Suction filtration, recrystallization from ethyl acetate, yield 76.18%.

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Abstract

The invention relates to a preparation method of 2-chloro-3-formyl quinoline derivatives. The preparation method comprises the following steps: by taking acetanilide or substituted acetanilide as a raw material, reacting with bis(trichloromethyl) carbonate (BTC) and N,N-dimethylformamide (DMF) in an organic solvent to obtain a target compound. The preparation method provided by the invention has the advantages that bis(trichloromethyl) carbonate is adopted for replacing a phosphorus-containing or sulfur-containing chlorination reagent, so that the problems of treatment of phosphorus-containing or sulfur-containing byproducts and wastewater discharge in a production process are solved, the preparation method has the characteristics that raw materials are easily available, the cost is low, operation steps are simple, reaction conditions are mild, the energy consumption is low, the reaction process is safe, the environmental pollution is small and the clean production can be realized, and the preparation method has industrialization application prospect.

Description

technical field [0001] The invention relates to a preparation method of quinoline derivatives, in particular to the preparation of 2-chloro-3-methanol with bistrichloromethyl carbonate BTC, N,N-dimethylformamide DMF, acetanilide or substituted acetanilide A method for acyl quinoline derivatives. Background technique [0002] Heterocyclic compounds containing quinoline skeletons, as important nitrogen-containing aromatic heterocyclic compounds, widely exist in natural products and exhibit significant biological activities, such as antibacterial, antiviral, antitumor, antiallergic, antiasthma, antihypertensive Blood pressure, enhance memory, antidepressant, etc. At the same time, as an important chemical raw material, it has been widely used in organic synthesis, drug synthesis, material chemistry and other fields. 2-Chloro-3-formyl quinoline derivatives have chlorine and formyl active functional groups, which can be easily converted into other quinoline heterocyclic compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18
CPCC07D215/18
Inventor 但飞君郑星星韩雅莲孙铭皓刘璐璐
Owner CHINA THREE GORGES UNIV
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