The Synthetic Routes of 6-Chloro-N-(3-methoxypropyl)pyridazin-3-amine

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The Synthetic Routes of 6-Chloro-N-(3-methoxypropyl)pyridazin-3-amine: A Comprehensive Overview

Introduction:

6-Chloro-N-(3-methoxypropyl)pyridazin-3-amine is an important chemical compound that has found widespread use in the pharmaceutical industry.
It is commonly used as an intermediate in the synthesis of various drugs, including anti-hypertensive, anti-diabetic and anti-depressant agents.
The chemical structure of 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine is relatively complex, and its synthesis requires the use of various chemical reactions and steps.
This article provides a comprehensive overview of the synthetic routes to 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine, including the common methods and reagents used in its synthesis.

Chemical Properties:

6-Chloro-N-(3-methoxypropyl)pyridazin-3-amine is a white to off-white solid that is slightly soluble in water and highly soluble in organic solvents.
The molecule has a slightly bitter taste, and its chemical properties make it highly reactive to various reagents, including acids, bases, and reducing agents.
Its chemical stability is moderate, and it can undergo various chemical reactions, such as substitution, reduction, and oxidation, depending on the conditions of the reaction.

Synthetic Routes:

There are several synthetic routes to 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine, and the choice of route depends on the available reagents, equipment, and the desired yield and purity of the product.
The following are some of the common synthetic routes to 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine:

Route 1: The Pinner Reaction

The Pinner reaction is a commonly used method for the synthesis of 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine.
In this reaction, 3-methoxypropylamine and m-chloroperbenzoic acid are reacted in the presence of a solvent, such as acetone or DMSO, to produce the desired amine.
The reaction proceeds through a series of steps, including the formation of an imine intermediate, which is then reduced to form the amine.
The product can be further purified by crystallization or chromatography.

Route 2: The Leuckart Reaction

The Leuckart reaction is another commonly used method for the synthesis of 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine.
In this reaction, N-bromosuccinimide is used as the brominating agent, and the reaction is carried out in the presence of a solvent, such as benzene or toluene.
The reaction proceeds through a series of steps, including the formation of a bromide intermediate, which is then converted to the desired amine.
The product can be further purified by crystallization or chromatography.

Route 3: The Smiles Reaction

The Smiles reaction is another widely used method for the synthesis of 6-chloro-N-(3-methoxypropyl)pyridazin-3-amine.
In this reaction, 3-methoxypropyl chloride is reacted with sodium azide in the presence of a solvent, such as DMF or