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3-Chloro-6-ethoxy-pyridazine is a commonly used pharmaceutical intermediate and research chemical, with a wide range of applications in the pharmaceutical and chemical industry.
The synthetic routes of this compound have been widely studied and developed over the years, with several methods for its synthesis available.
One of the most common methods of synthesizing 3-chloro-6-ethoxy-pyridazine is through the reaction of pyridazine-3-carboxylic acid chloride with ethyl 3-aminopyrrolidone-2-carboxylate.
This reaction involves the nucleophilic substitution of the amine in the second amino acid with the carboxylate in the first, forming an intermediate amide, which then undergoes dehydration to form the desired N-carbamoyl derivative.
Another method for synthesizing 3-chloro-6-ethoxy-pyridazine involves the reaction of N-(2-chloroethyl)-3-nitropyridine-2,6-diamine with sodium hydroxide, followed by hydrolysis of the resulting N-nitroso compound with sodium hydroxide.
This method involves the nucleophilic substitution of the chloride in the secondary amine with the nitroso group in the primary amine, forming an intermediate nitroso compound, which is then reduced with hydroxide and finally hydrolyzed to form the desired N-carbamoyl derivative.
A third method for synthesizing 3-chloro-6-ethoxy-pyridazine involves the reaction of 2-(chloromethyl)pyridine with ethyl isocyanoacetate in the presence of a base, such as sodium hydroxide.
This reaction involves the nucleophilic substitution of the chloride in the primary amine with the isocyano group in the secondary amine, forming an intermediate isocyanate, which then undergoes substitution with the chloride in the presence of an base to form the desired N-carbamoyl derivative.
All of these synthetic routes are relatively straightforward and have been used to synthesize 3-chloro-6-ethoxy-pyridazine on a large scale.
However, some of these methods may be more efficient or cost-effective than others, depending on the specific needs and parameters of the synthesis process.
Additionally, some of these methods may require more advanced equipment or specialized conditions, such as the use of hazardous reagents or solvents.
Therefore, it is important to carefully evaluate the synthetic route and consider the specific needs of the synthesis process when choosing a method for synthesizing 3-chloro-6-ethoxy-pyridazine.