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7-Amino-4-methyl-2-quinolinone is an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products.
The synthesis of this compound has been widely studied, and several synthetic routes have been reported in the literature.
In this article, we will discuss some of the most commonly used synthetic routes for the synthesis of 7-amino-4-methyl-2-quinolinone.
One of the most commonly used methods for the synthesis of 7-amino-4-methyl-2-quinolinone is the Madison-Kuhn synthesis, which involves the reduction of 2-nitroquinoline-4-sulfenamide with lithium aluminum hydride (LiAlH4) to form the amine, followed by treatment with 4-methyl-2-oxo-2H-chromene-3-carbaldehyde to form the desired quinoline.
Another commonly used method for the synthesis of 7-amino-4-methyl-2-quinolinone is the Knoevenagel condensation, which involves the condensation of 2-nitro-2H-quinazoline with acetyl chloride or acetic anhydride in the presence of a Base such as pyridine or triethylamine to form the quinoline, followed by reduction to the desired amine.
A third method for the synthesis of 7-amino-4-methyl-2-quinolinone is the Halcon synthesis, which involves the condensation of 2-chlor-6-nitroquinoxaline-5-carboxylic acid with 3-methyl-1,2,4-oxadiazole-5-carboxylic acid in the presence of pyridine to form the quinoline, followed by reduction to the desired amine.
A fourth method for the synthesis of 7-amino-4-methyl-2-quinolinone is the P2P (Pyrrole-2-Pyrrolidone) synthesis, which involves the condensation of 2-nitro-4-methyl-2H-quinazoline with 4-methyl-2-oxo-2H-chromene-3-carbaldehyde in the presence of a base such as triethylamine to form the quinoline, followed by reduction to the desired amine.
A fifth method for the synthesis of 7-amino-4-methyl-2-quinolinone is the Mannich reaction, which involves the condensation of 2-aminopyridine with 2-chloro-6-nitroquinoxaline-5-carboxylic acid in the presence ofadded base such as sodium hydroxide, to form the quinoline, followed by reduction to the desired amine.
It is important to note that these are just a few examples of synthetic routes for the synthesis of 7-amino-4-methyl-2-quinolinone, and there are many other methods that have been reported in the literature.
The choice of synthetic route will depend on several factors, such as the availability of reagents, the desired yield, and the purity of the desired product.
In conclusion, 7-amino-4-methyl-2-quinolinone is an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products, and several synthetic routes have been reported in the literature for its synthesis, including the Madison-Kuhn synthesis, the Knoevenagel condensation, the Halcon synthesis, the P2P synthesis and the Mannich reaction.
The choice of the synthetic route will depend on several factors, such as the availability of reagents, the