The Synthetic Routes of Methyl 3,6-dichloropyridazine-4-carboxylate

Methyl 3,6-dichloropyridazine-4-carboxylate is a versatile organic compound with a wide range of applications in the chemical industry.
Its synthetic routes, however, can be complex and challenging, requiring careful selection of reagents and reaction conditions.
In this article, we will explore the various synthetic routes of methyl 3,6-dichloropyridazine-4-carboxylate, focusing on the most common methods used in the chemical industry.

One of the most common methods of synthesizing methyl 3,6-dichloropyridazine-4-carboxylate involves the use of anhydrous ammonia as a reagent.
The reaction is carried out in the presence of a strong acid catalyst, such as sulfuric acid, and involves the nitration of 3,6-dichloropyridazine-4-carboxaldehyde, which is then followed by treatment with ammonia.
The reaction can be summarized as follows:

3,6-dichloropyridazine-4-carboxaldehyde + NH3 + H2SO4 → Methyl 3,6-dichloropyridazine-4-carboxylate + NH2OH

Another method of synthesizing methyl 3,6-dichloropyridazine-4-carboxylate involves the use of chloroformic acid as a reagent.
The reaction is carried out in the presence of a strong base catalyst, such as sodium hydroxide, and involves the chlorination of 3,6-dichloropyridazine-4-carboxylic acid, which is then followed by treatment with chloroformic acid.
The reaction can be summarized as follows:

3,6-dichloropyridazine-4-carboxylic acid + 2 CHCl3 → Methyl 3,6-dichloropyridazine-4-carboxylate + 2 CCl4 + 2 NaOH

A third method of synthesizing methyl 3,6-dichloropyridazine-4-carboxylate involves the use of thionyl chloride as a reagent.
The reaction is carried out in the presence of a strong acid catalyst, such as sulfuric acid, and involves the chlorination of 3,6-dichloropyridazine-4-carboxaldehyde, which is then followed by treatment with thionyl chloride.
The reaction can be summarized as follows:

3,6-dichloropyridazine-4-carboxaldehyde + SO2Cl2 → Methyl 3,6-dichloropyridazine-4-carboxylate + 2 SO2 + 2 HCl

Finally, methyl 3,6-dichloropyridazine-4-carboxylate can also be synthesized through a two-step reaction involving the use of 3-chlorocinnamic acid as a reagent.
In the first step, the acid is treated with 2-nitropropane in the presence of a strong acid catalyst, such as sulfuric acid, to form 3-chlorocinnamic acid nitrate.
In the second step, the nitrate is then treated with sodium hydroxide to form methyl 3,6-dichloropyridazine-4-carboxylate.
The reaction can be summarized as follows:

3-chlorocinnamic acid + 2 NO2C4H9 → 3-chlorocinnamic acid nitrate + 2 NO2 + HCl
3-chlorocinnamic acid nitrate + NaOH → Methyl 3,6-dichloropyridazine-4-carboxylate + NaNO3 + H2O

In conclusion, methyl 3,