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Imidazo[1,2-b]pyridazin-6-amine, 2-methyl- (9CI) is a synthetic compound that has various applications in the chemical industry.
This compound is commonly used as a building block for the synthesis of other chemicals and drugs.
The synthetic routes to 9CI can be broadly classified into two categories: traditional and modern synthesis routes.
Traditional Synthetic Routes:
The traditional synthetic routes to 9CI involve several steps and require the use of several reagents.
The most commonly used traditional method involves the synthesis of imidazole followed by the addition of a diazo compound to form the imidazo[1,2-b]pyridazin-6-amine skeleton.
The first step in the traditional synthesis of 9CI involves the synthesis of imidazole.
This can be achieved by the reduction of benzoic acid with sodium in the presence of benzaldehyde, or by the condensation of oxalic acid with sodium hydroxide in the presence of methyl orange.
In the second step, a diazo compound is added to the imidazole ring to form the imidazo[1,2-b]pyridazin-6-amine skeleton.
This can be achieved by the addition of diazo compounds such as para-nitrophenylenediamine, 4-nitrophenyl-2-diazo-5-oxopyrrolidine-1,2-dione or 2-methyl-5-nitro-1,3-oxazolidin-3-one to imidazole under basic conditions.
Modern Synthetic Routes:
The modern synthetic routes to 9CI are more efficient and economical than the traditional routes.
These routes involve the use of newer reagents and catalysts, and can be carried out in a shorter period of time.
Some of the modern synthetic routes to 9CI are outlined below:
- Synthesis of 9CI via a diazo compound: 2-methyl-5-nitro-1,3-oxazolidin-3-one can be used as a diazo compound for the synthesis of 9CI.
The synthesis involves the reaction of 2-methyl-5-nitro-1,3-oxazolidin-3-one with imidazole under basic conditions followed by the oxidation of the resulting compound to form 9CI. - Synthesis of 9CI via a redox reaction: 9CI can be synthesized via a redox reaction between 2-methyl-5-nitro-1,3-oxazolidin-3-one and sodium metal in the presence of dimethylformamide (DMF) or dimethylacetamide (DMA).
- Synthesis of 9CI via a palladium-mediated reaction: 9CI can be synthesized via a palladium-mediated reaction between imidazole and a substituted aryl halide in the presence of a palladium catalyst and a base.
Advantages of the Synthetic Routes:
The synthetic routes to 9CI offer several advantages over traditional routes.
The modern routes are more efficient and economical as they require less time and fewer reagents.
The modern routes also involve the use of safer and more environmentally friendly reagents, making the process more sustainable.
Additionally, the modern routes offer greater control over the reaction conditions, resulting in a higher yield of the desired product.
Chemical Properties of 9CI:
9CI is a white solid that is soluble in water and organic solvents.
It is an intermediate compound that finds applications in the synthesis of other chemicals and drugs.
The compound has been shown to exhibit ant