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6-Chloropyridazine-3-carboxamide is an organic compound that is widely used in various applications in the chemical industry.
Its synthesis has been the subject of extensive research, with several synthetic routes being developed over the years.
The selection of a particular synthetic route depends on a variety of factors, including the desired yield, cost, and availability of starting materials.
In this article, we will discuss some of the synthetic routes that have been developed for the synthesis of 6-chloropyridazine-3-carboxamide.
- Route 1: via Chlorination of Pyridazine-3-carboxylic Acid
One of the most commonly used synthetic routes for the synthesis of 6-chloropyridazine-3-carboxamide involves the chlorination of pyridazine-3-carboxylic acid.
The reaction involves treating pyridazine-3-carboxylic acid with chlorine gas or a chlorinating agent such as thionyl chloride.
The reaction is typically carried out in the presence of a solvent such as ether or dichloromethane.
The product is then isolated by treatment with a base such as sodium bicarbonate or sodium carbonate.
This route is relatively simple and straightforward, and can be easily scaled up for industrial production.
- Route 2: via Coupling of Pyridine-3-carboxaldehyde and Chloramine-T
Another commonly used synthetic route involves the coupling of pyridine-3-carboxaldehyde with chloramine-T.
Pyridine-3-carboxaldehyde is first prepared by treating pyridine-3-carboxylic acid with paraformaldehyde in the presence of an acid catalyst such as hydrochloric acid.
The resulting pyridine-3-carboxaldehyde is then treated with chloramine-T in the presence of a solvent such as DMF or DMA.
The product is then isolated by treatment with sodium bicarbonate or sodium carbonate.
This route is also relatively simple and straightforward, and can be easily scaled up for industrial production.
- Route 3: via Nitrile-Cyanation of Pyridine-3-carboxylic Acid
A third synthetic route involves the nitrile-cyanation of pyridine-3-carboxylic acid.
The reaction involves treating pyridine-3-carboxylic acid with dicyanic acid or a similar nitrile-forming reagent.
The reaction is typically carried out in the presence of a solvent such as acetonitrile or dichloromethane.
The product is then isolated by treatment with a base such as sodium bicarbonate or sodium carbonate.
This route is also relatively simple and straightforward, and can be easily scaled up for industrial production.
- Route 4: via Decarboxylative Coupling of Pyridine-3-carboxylic Acid with Amino Chloride
A fourth synthetic route involves the decarboxylative coupling of pyridine-3-carboxylic acid with an amino chloride such as chloramine-T.
The reaction is typically carried out in the presence of a solvent such as DMF or DMA.
The product is then isolated by treatment with sodium bicarbonate or sodium carbonate.
This route requires careful optimization of reaction conditions, but can provide a useful alternative to other synthetic routes.
In conclusion, there are several synthetic routes that have been developed for the synthesis of 6-chloropyridazine-3-carboxamide.
The selection of a particular route depends on a variety of factors, including the desired yield, cost, and availability of starting materials.
Each of the routes described above is relatively simple and straightforward, and can be easily scaled up for industrial production.
The choice of route will depend on the specific requirements