The Synthetic Routes of 6-[(3-Methoxyphenyl)methyl]-3-pyridazinamine

The synthesis of 6-[(3-Methoxyphenyl)methyl]-3-pyridazinamine, commonly referred to as MPP, is an important compound in the chemical industry.
This compound has a wide range of applications in various fields such as pharmaceuticals, agrochemicals, and materials science.
MPP can be synthesized through several methods, and this article will discuss the most commonly used synthetic routes.

Route 1:via the reaction of 3-formyl-1H-pyrazole with 3-methoxyphenylboronic acid

The first route starts with the reaction of 3-formyl-1H-pyrazole with 3-methoxyphenylboronic acid in the presence of a palladium catalyst.
This reaction leads to the formation of MPP in good yield.
The advantages of this route are the availability of the starting materials and the mild reaction conditions, which make it a popular choice in the industry.

Route 2:via the reaction of 3-[(3-methoxyphenyl)methylidene]-1H-pyrazole with nitrous acid

The second route involves the reaction of 3-[(3-methoxyphenyl)methylidene]-1H-pyrazole with nitrous acid to form MPP.
This reaction is commonly known as a nitrating reaction and requires the use of a strong acid catalyst such as sulfuric acid.
This route is less common compared to the first route due to the use of hazardous reagents such as nitrous acid.

Route 3:via the reaction of 4-nitro-3-methoxyphenylamine with hydrazine

The third route starts with the reaction of 4-nitro-3-methoxyphenylamine with hydrazine in the presence of a basic catalyst such as sodium hydroxide.
This reaction leads to the formation of MPP in good yield.
The advantage of this route is that it does not require the use of hazardous reagents such as nitrous acid.

Route 4:via the reaction of 4-chloro-3-methoxyphenylamine with hydrazine

The fourth route involves the reaction of 4-chloro-3-methoxyphenylamine with hydrazine to form MPP.
This reaction is similar to the third route and requires the use of a basic catalyst such as sodium hydroxide.
The advantage of this route is the availability of the starting material 4-chloro-3-methoxyphenylamine, which is easier to obtain than 4-nitro-3-methoxyphenylamine.

Route 5:via the reaction of 3-methoxy-1H-pyrazole-5-carbaldehyde with sodium azide and sodium cyanide

The fifth route involves the reaction of 3-methoxy-1H-pyrazole-5-carbaldehyde with sodium azide and sodium cyanide in the presence of a base such as sodium hydroxide.
This reaction leads to the formation of MPP in good yield.
The advantage of this route is that it avoids the need for a nitrating reaction, which can be hazardous.

In conclusion, the synthesis of MPP is possible through several routes, each with its advantages and disadvantages.
The choice of route depends on the availability of starting materials, the reaction conditions, and the hazardous nature of the reagents.
The most commonly used routes include the reaction of 3-formyl-1H-pyrazole with 3-methoxyphenylboronic acid and the reaction of 3-[(3-methoxyphenyl)methylidene]-1H-pyrazole with nitrous acid.