The Synthetic Routes of 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE

4-Chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile is a synthetic compound that has a wide range of applications in the chemical industry.
This compound is commonly used as an intermediate in the production of various pharmaceuticals, agrochemicals, and industrial chemicals.
In this article, we will discuss the synthetic routes of 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile, including the traditional route and the more recent advancements in synthesis methods.

Traditional Synthetic Route

The traditional synthetic route for 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile involves a multi-step process that involves several chemical reactions.
The synthesis of this compound typically starts with the reaction of chloroacetic acid with sodium hydroxide to form 3-chloro-3-oxopropanenitrile.
This is then followed by a reaction with propyl bromide and sodium hydroxide to form 3-bromo-3-propoxypropanenitrile.

The next step in the synthesis involves the reaction of 3-bromo-3-propoxypropanenitrile with 6-methoxyquinoline-3-carbonitrile hydrochloride in the presence of a solvent such as dichloromethane.
This reaction results in the formation of 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile, which can then be further purified and isolated using conventional methods.

Advanced Synthetic Routes

In recent years, there have been several advancements in the synthetic route for 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile.
One of the most widely used advanced methods is the Suzuki-Miyaura coupling reaction.
This reaction involves the use of boron trifluoride ether and a palladium catalyst to coupling 3-chloro-3-oxopropanenitrile and 6-methoxyquinoline-3-carbonitrile in the presence of a solvent such as toluene.
The result of this reaction is the formation of 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile, which can then be further purified and isolated using conventional methods.

Another advanced method for the synthesis of 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile is the Stille coupling reaction.
This reaction involves the use of a metal catalyst such as rhodium and a ligand such as tris(dibenzylideneacetone)dipalladium(0) to couple 3-chloro-3-oxopropanenitrile and 6-methoxyquinoline-3-carbonitrile in the presence of a solvent such as toluene.
The result of this reaction is the formation of 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile, which can then be further purified and isolated using conventional methods.

Applications

4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile is used as an intermediate in the production of various pharmaceuticals, agrochemicals