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2-Chloro-3-formyl-6-methylquinoline is a important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products.
It is widely used as a building block for the synthesis of antibiotics, anti-inflammatory drugs, and herbicides.
The synthesis of 2-chloro-3-formyl-6-methylquinoline can be achieved through several different routes, including synthetic routes.
One of the most common synthetic routes for the synthesis of 2-chloro-3-formyl-6-methylquinoline is the Ullmann reaction.
This reaction involves the condensation of 3-methyl-2-butenal with chloroform in the presence of a transition metal catalyst, such as copper salts.
The reaction proceeds through an enolate intermediate, which is generated from the 3-methyl-2-butenal.
The enolate then undergoes an intramolecular electrophilic substitution reaction with the chloroform, resulting in the formation of 2-chloro-3-formyl-6-methylquinoline.
Another synthetic route for the synthesis of 2-chloro-3-formyl-6-methylquinoline is the hydrolysis of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline.
This reaction involves the hydrolysis of the nitro group of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline using a strong acid catalyst, such as sulfuric acid.
The resulting intermediate is then treated with a base, such as sodium hydroxide, to form the formylate salt.
The formylate salt is then hydrolyzed using a weak acid, such as acetic acid, to release 2-chloro-3-formyl-6-methylquinoline.
Another route is the Reduction of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline.
This reaction involves the reduction of the nitro group of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline using a reducing agent, such as hydride reagents, lithium aluminum hydride (LiAlH4), or diisobutylaluminum hydride (DIBAL-H).
The resulting intermediate is then treated with a base, such as sodium hydroxide, to form the formylate salt.
The formylate salt is then hydrolyzed using a weak acid, such as acetic acid, to release 2-chloro-3-formyl-6-methylquinoline.
In conclusion, 2-chloro-3-formyl-6-methylquinoline can be synthesized through several different routes, including synthetic routes, such as the Ullmann reaction, hydrolysis of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline, and reduction of 2-chloro-6-methyl-3-nitro-5-oxo-quinoline.
Each of these routes has its own advantages and disadvantages, and the choice of route will depend on factors such as the availability of reagents, the scale of the synthesis, and the desired purity of the final product.