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5-Iodo-3(2H)-pyridazinone is an organic compound that is commonly used as a building block in the production of various chemicals and pharmaceuticals.
The production process of 5-Iodo-3(2H)-pyridazinone involves several steps, which are outlined below.
- Synthesis of 2-bromo-3-nitropyridine
The first step in the production of 5-Iodo-3(2H)-pyridazinone is the synthesis of 2-bromo-3-nitropyridine.
This compound is synthesized by treating 2-bromo-3-aminopyridine with nitrous acid.
The reaction is exothermic and requires careful monitoring to avoid excessive heating. - Reduction of 2-bromo-3-nitropyridine to 2-bromo-3-nitropyridane
Next, the 2-bromo-3-nitropyridine is reduced to 2-bromo-3-nitropyridane using a reducing agent such as lithium aluminum hydride (LiAlH4).
This step is necessary to reduce the nitro group to an amino group. - Condensation of 2-bromo-3-nitropyridane with Malonic acid
In the next step, the 2-bromo-3-nitropyridane is condensed with malonic acid in the presence of a condensing agent such as dicyclohexylcarbodiimide (DCC).
This reaction results in the formation of a diester, which is then hydrolyzed using sodium hydroxide to yield 3-bromo-2-pyridinecarboxylic acid. - Nitration of 3-bromo-2-pyridinecarboxylic acid
The 3-bromo-2-pyridinecarboxylic acid is then nitrated using nitric acid to yield 3-bromo-2-pyridinecarboxylic acid nitrate. - Reduction of 3-bromo-2-pyridinecarboxylic acid nitrate to 3-bromo-2-pyridinecarboxylic acid
The 3-bromo-2-pyridinecarboxylic acid nitrate is reduced to 3-bromo-2-pyridinecarboxylic acid using a reducing agent such as lithium aluminum hydride (LiAlH4). - Halogenation of 3-bromo-2-pyridinecarboxylic acid
The 3-bromo-2-pyridinecarboxylic acid is then halogenated using Iodine and a solvent such as carbon tetrachloride.
This step results in the formation of 3-bromo-5-iodo-2-pyridinecarboxylic acid. - Dehydration of 3-bromo-5-iodo-2-pyridinecarboxylic acid
The next step is to remove water from the 3-bromo-5-iodo-2-pyridinecarboxylic acid using a dehydrating agent such as phosphorus trichloride.
This step is necessary to prevent the formation of unwanted side products during the subsequent steps. - Reduction of 3-bromo-5-iodo-2-pyridinecarboxylic acid to 5-iodo-3(2H)-pyridazinone
Finally, the 3-bromo-5-iodo-2-pyridinecarboxylic acid is reduced to 5-iodo-3(2H)-pyridazinone using a reducing agent such as lithium aluminum hydride (LiAlH4).
This step requires careful