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6-Methyl-3(2H)-pyridazinone is an important organic compound that is widely used in the chemical industry.
It is a heterocyclic compound with a six-membered aromatic ring fused to a three-membered pyridazinone ring.
The compound is derived from the condensation of 2-methylthiophenol and 3-hydroxy-2-methylpyridine.
In the chemical industry, there are several synthetic routes to 6-methyl-3(2H)-pyridazinone, each with its own advantages and disadvantages.
The following are the most commonly used synthetic routes:
- Synthesis via the Robinson-Claisen reaction
The Robinson-Claisen reaction is a common method for the synthesis of 6-methyl-3(2H)-pyridazinone.
This reaction involves the condensation of 2-methylthiophenol with 3-hydroxy-2-methylpyridine in the presence of a strong acid catalyst, such as sulfuric acid or phosphoric acid.
The reaction proceeds through an enolate intermediate, which is formed by treatment of the phenol with an alkali metal hydroxide.
The presence of the sulfur atom in the starting material results in the formation of the desired pyridazinone ring.
The Robinson-Claisen reaction is a highly efficient method for the synthesis of 6-methyl-3(2H)-pyridazinone, and it allows for the synthesis of the compound in high yields.
However, it can be hazardous to handle the reagents and heat generated during the reaction, and it requires careful monitoring of the reaction conditions.
- Synthesis via the Grignard reaction
The Grignard reaction is another common method for the synthesis of 6-methyl-3(2H)-pyridazinone.
This reaction involves the treatment of 2-methylthiophenol with a magnesium halide reagent, such as magnesium bromide or magnesium iodide.
The resulting Grignard reagent is then treated with a base, such as potassium hydroxide or sodium hydroxide, to form the desired pyridazinone ring.
The Grignard reaction is a highly efficient method for the synthesis of 6-methyl-3(2H)-pyridazinone, and it allows for the synthesis of the compound in high yields.
However, it requires careful handling of the reagents, and it can generate unwanted byproducts if the reaction conditions are not carefully controlled.
- Synthesis via the Ullmann reaction
The Ullmann reaction is a common method for the synthesis of 6-methyl-3(2H)-pyridazinone.
This reaction involves the condensation of 2-methylthiophenol with 3-hydroxy-2-methylpyridine in the presence of a metal catalyst, such as copper or zinc.
The reaction proceeds through an enolate intermediate, which is formed by treatment of the phenol with an alkali metal hydroxide.
The presence of the metal catalyst is crucial for the formation of the desired pyridazinone ring.
The Ullmann reaction is a highly efficient method for the synthesis of 6-methyl-3(2H)-pyridazinone, and it allows for the synthesis of the compound in high yields.
However, it requires careful handling of the reagents and the metal catalyst, and it can generate unwanted byproducts if the reaction conditions are not carefully controlled.
In conclusion, there are several synthetic routes to 6-methyl-3(2H)-pyridazinone, including the Robinson-Claisen reaction, the Grignard reaction, and the Ullmann reaction.
Each of these
