The Synthetic Routes of 3-Isoquinolinecarboxylic acid, ethyl ester

3-Isoquinolinecarboxylic acid, ethyl ester is an important chemical intermediate in the pharmaceutical and agrochemical industries.
It is used as a starting material for the synthesis of various active pharmaceutical ingredients and pesticides.
The synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester can be achieved through several routes, both synthetic and natural.
In this article, we will discuss some of the synthetic routes for the synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester.

One of the most commonly used synthetic routes for the synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester is the Houben-van der Kwast-Kraemer (HVK) hydrolysis of 3-chloro-2-hydroxy-N-phenyl-acetamide.
This route involves the nucleophilic substitution of the chloride group in 3-chloro-2-hydroxy-N-phenyl-acetamide with a molecule of water, leading to the formation of the corresponding carboxylic acid.
The carboxylic acid is then esterified with ethanol to give 3-Isoquinolinecarboxylic acid, ethyl ester.

Another synthetic route for the synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester is the reaction of 3-bromo-N-phenyl-acetamide with sodium hydroxide in aqueous dioxane.
The bromide group in 3-bromo-N-phenyl-acetamide is nucleophilically substituted by the water molecule, leading to the formation of the carboxylic acid.
The carboxylic acid is then esterified with ethanol to give 3-Isoquinolinecarboxylic acid, ethyl ester.

A third synthetic route for the synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester is the reaction of N-phenyl-acetamide with phosphorus trichloride in the presence of a Lewis acid catalyst such as aluminum chloride.
The acetamide group in N-phenyl-acetamide is first transformed into a cyclic imide by dehydration, followed by rearrangement to the corresponding isocyanate.
The isocyanate is then reacted with ethanol to give 3-Isoquinolinecarboxylic acid, ethyl ester.

In addition to these synthetic routes, 3-Isoquinolinecarboxylic acid, ethyl ester can also be synthesized through natural routes such as the extraction of the natural product from the plant or microorganism from which it is derived.
This is typically done using solvents such as methanol or ethanol, followed by esterification with ethanol.

Overall, the synthesis of 3-Isoquinolinecarboxylic acid, ethyl ester can be achieved through a variety of synthetic routes, each with its own advantages and disadvantages.
The specific route chosen will depend on factors such as the availability and cost of starting materials, the desired product yield, and the specific requirements of the application.