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6-Chloro-5-methylpyridazin-3-amine is an organic compound that is commonly used in various applications in the chemical industry.
The synthesis of this compound can be achieved through several different methods, each of which has its own advantages and disadvantages.
In this article, we will discuss the three most commonly used synthetic routes for 6-chloro-5-methylpyridazin-3-amine and their corresponding benefits and drawbacks.
Route 1: Nitrile-Amine Oxidation
The first synthetic route for 6-chloro-5-methylpyridazin-3-amine involves the nitrile-amine oxidation method.
This method involves the conversion of a nitrile to an amine using oxidizing agents such as hydrogen peroxide or sodium hypochlorite.
The reaction begins by the nitrilization of a primary amine with a nitrile, followed by the oxidation of the resulting amide to the corresponding amine.
The resulting amine is then chlorinated using chlorine or a chlorinating agent to yield 6-chloro-5-methylpyridazin-3-amine.
Advantages:
- This method is relatively simple and can be carried out using easily available reagents.
- The reaction can be carried out at room temperature, which reduces the risk of side reactions and allows for the use of less expensive equipment.
- The nitrile-amine oxidation method can be performed in a single-step reaction, which reduces the number of steps required for the synthesis of 6-chloro-5-methylpyridazin-3-amine.
Disadvantages:
- The reaction can be sensitive to the solvent used, and the choice of solvent must be carefully considered to ensure the desired product is obtained.
- The reaction is not highly selective, and a range of by-products can be formed depending on the reaction conditions.
- The reaction can be hazardous due to the use of oxidizing agents and chlorine.
Route 2: Chlorination of an Amide
The second synthetic route for 6-chloro-5-methylpyridazin-3-amine involves the chlorination of an amide.
This method involves the conversion of an amide to a chloride using chlorine or a chlorinating agent.
The chloride can then be converted to the corresponding amine using a reducing agent such as lithium aluminum hydride (LiAlH4).
The resulting amine can then be further processed to yield 6-chloro-5-methylpyridazin-3-amine.
Advantages:
- This method allows for the synthesis of 6-chloro-5-methylpyridazin-3-amine using a one-step reaction, making it relatively simple and efficient.
- The reaction can be carried out at moderate temperatures and pressures, which reduces the risk of side reactions and allows for the use of less expensive equipment.
- The reaction is highly selective, allowing for the formation of the desired product in high yield.
Disadvantages:
- The reaction requires the use of chlorinating agents, which can be hazardous and difficult to handle.
- The reaction requires the use of reducing agents such as lithium aluminum hydride, which can be expensive and difficult to handle.
- The reaction can be sensitive to the solvent used, and the choice of solvent must be carefully considered to ensure the desired product is obtained.
Route 3: Reductive Amination
The third synthetic route for 6-chloro-5-methylpyridazin-3-amine involves the reductive amination method.
This method involves the reduction of a nitrile to an amine using reducing agents such as