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4-Pyridazinemethanamine is an important organic compound that finds applications in various fields of the chemical industry.
Its synthetic routes are not only varied but also versatile, making it a synthetic target of great interest.
This article provides an overview of the various synthetic routes to 4-pyridazinemethanamine, including the traditional and modern methods employed in its synthesis.
The traditional synthetic routes
The traditional synthetic routes to 4-pyridazinemethanamine include the following:
The R.
P.
way
The R.
P.
way involves the reduction of 4-nitrophenylacetamide to form 4-nitrophenylacetaldehyde, which is then reduced further to form 4-nitrophenylactic acid.
The acid is then converted to 4-pyridazinemethanamine through the following steps:
- Hydrolysis of the 4-nitrophenylactic acid to form 4-nitrophenylacetic acid
- Oxidation of the 4-nitrophenylacetic acid to form 4-nitrophenylazetidine-3-one
- Reduction of the 4-nitrophenylazetidine-3-one to form 4-pyridazinemethanamine
The H.
W.
way
The H.
W.
way involves the reduction of 4-nitrophenylazo-2,4-dinitrobenzene to form 4-nitrophenylacetic acid.
The acid is then converted to 4-pyridazinemethanamine through the following steps:
- Hydrolysis of the 4-nitrophenylacetic acid to form 4-nitrophenylacetic acid
- Reduction of the 4-nitrophenylacetic acid to form 4-pyridazinemethanamine
The Mannich reaction
The Mannich reaction involves the condensation of formaldehyde, acetaldehyde, and ammonia to form 4-pyridazinemethanamine.
The reaction is carried out in the presence of a base, such as sodium hydroxide, and is followed by hydrolysis of the resulting intermediate to form 4-pyridazinemethanamine.
The modern synthetic routes
The modern synthetic routes to 4-pyridazinemethanamine include the following:
The palladium-catalyzed cross-coupling reaction
The palladium-catalyzed cross-coupling reaction involves the reaction of an aryl halide with an arylboronic acid in the presence of a palladium catalyst.
The reaction produces 4-pyridazinemethanamine, which can be further purified and used as desired.
The Sonogashira reaction
The Sonogashira reaction involves the condensation of an aryl halide with a phenyl acetate in the presence of a palladium catalyst.
The reaction produces 4-pyridazinemethanamine, which can be further purified and used as desired.
The Stille reaction
The Stille reaction involves the condensation of an aryl halide with a phenyl dichloride in the presence of a palladium catalyst.
The reaction produces 4-pyridazinemethanamine, which can be further purified and used as desired.
Advantages of modern synthetic routes
The modern synthetic routes to 4-pyridazinemethanamine offer several advantages over the traditional methods.
Firstly, they are more efficient, as they allow for the synthesis of 4-pyridazinemethanamine in a shorter period of time.
Secondly