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The synthesis of 2-acetyl-4,5-dichloro-3(2H)-pyridazinone is an important process in the chemical industry, as this compound is widely used as an intermediate in the production of various pharmaceuticals, agrochemicals, and other chemical products.
There are several synthetic routes for the preparation of 2-acetyl-4,5-dichloro-3(2H)-pyridazinone, each with its own advantages and disadvantages.
One of the most common synthetic routes for the synthesis of 2-acetyl-4,5-dichloro-3(2H)-pyridazinone is the "classical route", which involves several steps and the use of hazardous reagents.
This route involves the following steps:
- Preparation of 4-chloro-3-nitroaniline: This compound is prepared by treating 3-nitroaniline with chloroform and a catalytic amount of ferric chloride.
- Reduction of 4-chloro-3-nitroaniline to 4-aminodye: This step is carried out by reducing the chlorinated aniline with a reducing agent such as tin(II) chloride in the presence of sodium hydroxide.
- Nitration of 4-aminodye to 4-nitroaminodye: This is accomplished by treating 4-aminodye with nitric acid and a catalytic amount of hydrochloric acid.
- Condensation of 4-nitroaminodye with acetyl chloride: This step involves the condensation of 4-nitroaminodye with acetyl chloride in the presence of a catalyst such as aluminum chloride.
- Dechlorination of the resulting compound: This step involves treating the condensed compound with a dechlorinating agent such as potassium permanganate to remove the chlorine atoms and leave the final product, 2-acetyl-4,5-dichloro-3(2H)-pyridazinone.
An alternative route for the synthesis of 2-acetyl-4,5-dichloro-3(2H)-pyridazinone is the "microwave-assisted route", which involves using microwave irradiation to accelerate the reaction kinetics and simplify the synthetic process.
This route involves the following steps:
- Preparation of a solution of 3-nitroaniline in acetonitrile: This compound is prepared by dissolving 3-nitroaniline in acetonitrile.
- Addition of acetyl chloride to the solution of 3-nitroaniline: This step involves adding acetyl chloride to the solution of 3-nitroaniline.
- Microwave irradiation of the solution: The solution is subjected to microwave irradiation for a certain period of time to initiate the reaction.
- Recovery of the product: The resulting product is extracted from the reaction mixture and purified by standard methods.
A third route for the synthesis of 2-acetyl-4,5-dichloro-3(2H)-pyridazinone is the "hydrothermal route", which involves the use of water as a reaction solvent and the elimination of the need for hazardous reagents.
This route involves the following steps:
- Preparation of a mixture of 3-nitroaniline, sodium nitrite, and water: This mixture is prepared by dissolving 3-nitroaniline and sodium nitrite in water.
- Heating of the mixture: The mixture is heated to a certain temperature for a certain