The Synthetic Routes of Methyl 3-chloropicolinate

Methyl 3-chloropicolinate is a chemical compound that finds extensive use in the chemical industry due to its unique properties and versatile applications.
The compound is widely used as an intermediate in the production of various chemicals, drugs, and other products.
In this article, we will discuss the synthetic routes of Methyl 3-chloropicolinate, which are widely used in the chemical industry.

Synthetic routes of Methyl 3-chloropicolinate

1. Chlorination of 3-Picoline

The most common synthetic route to Methyl 3-chloropicolinate is through the chlorination of 3-picoline.
This reaction is carried out by treating 3-picoline with chlorine gas in the presence of a catalyst like ferric chloride.
The reaction is exothermic and requires careful handling.
The product is then purified by recrystallization or distillation to remove any impurities.

2. Reduction of Chloro-3-picoline

Another route to Methyl 3-chloropicolinate is through the reduction of chloro-3-picoline.
This reaction is carried out by treating chloro-3-picoline with reducing agents like lithium aluminum hydride (LiAlH4) or hydrogen in the presence of a catalyst like palladium on barium carbonate.
The product is then purified by recrystallization or distillation to remove any impurities.

3. Reaction with Thionyl Chloride

Methyl 3-chloropicolinate can also be synthesized by treating 3-picoline with thionyl chloride in the presence of a Lewis acid catalyst like aluminum chloride.
The reaction is carried out at a low temperature and requires careful handling of the reagents.
The product is then purified by recrystallization or distillation to remove any impurities.

Synthesis of Methyl 3-chloropicolinate by Chlorination of 3-Picoline

The chlorination of 3-picoline is the most widely used synthetic route to Methyl 3-chloropicolinate.
The reaction is carried out by treating 3-picoline with chlorine gas in the presence of a catalyst like ferric chloride.
The reaction is exothermic and requires careful handling of the reagents.
The product is then purified by recrystallization or distillation to remove any impurities.

The reaction is typically carried out in the presence of a solvent like dioxane or water.
The reaction is monitored by TLC or GC to ensure complete consumption of the reagents.
The product is then isolated by recrystallization or distillation.
The yield of Methyl 3-chloropicolinate can be improved by using high-purity reagents and optimizing the reaction conditions.

Synthesis of Methyl 3-chloropicolinate by Reduction of Chloro-3-picoline

Methyl 3-chloropicolinate can also be synthesized by reducing chloro-3-picoline with reducing agents like lithium aluminum hydride (LiAlH4) or hydrogen in the presence of a catalyst like palladium on barium carbonate.
The reaction is carried out at a low temperature and requires careful handling of the reagents.

The reaction is typically carried out in the presence of a solvent like ethanol or ether.
The reaction is monitored by TLC or GC to ensure complete consumption of the reagents.
The product is then isolated by recrystallization or distillation.
The yield of Methyl 3-chloropicolinate can be improved by using high-purity reagents and optimizing the reaction conditions.