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6-Aminoisoquinoline is an important synthetic intermediate in the production of various pharmaceuticals, agrochemicals, and materials.
The demand for this compound has been increasing rapidly due to its diverse range of applications.
The following are some of the commonly used synthetic routes for the production of 6-aminoisoquinoline.
- The classic approach to synthesizing 6-aminoisoquinoline is through the Williamson ether synthesis, which involves the reduction of an aryl halide with lithium aluminum hydride (LiAlH4) in the presence of an ether solvent.
The reaction produces a secondary alcohol, which can then be converted into 6-aminoisoquinoline through a series of chemical transformations. - Another popular route to 6-aminoisoquinoline involves the reduction of an aryl nitrile with lithium alaninate in the presence of a solvent such as THF or DMF.
The reaction produces an amino acid, which can then be hydrolyzed to yield 6-aminoisoquinoline. - A more recent synthetic route to 6-aminoisoquinoline involves the use of transition metal catalysts such as palladium on barium sulfate or copper iodide.
The reaction involves the Suzuki-Miyaura cross-coupling reaction between an aryl boronic acid and an aryl halide in the presence of the transition metal catalyst. - Another method for synthesizing 6-aminoisoquinoline involves the use of organic reduction agents such as lithium aluminum hydride or diisobutylaluminum hydride (DIBAL-H).
The reduction reaction takes place in the presence of a polar protic solvent such as acetone or ethanol. - A recent advance in the synthesis of 6-aminoisoquinoline has been the use of microwave irradiation as a catalyst for the reaction.
The method involves the use of a transition metal catalyst such as palladium on barium sulfate or copper iodide, and the reaction takes place in the presence of a polar protic solvent such as acetone or ethanol.
The use of microwave irradiation greatly accelerates the reaction, reducing the time and cost required for synthesis.
In conclusion, the synthesis of 6-aminoisoquinoline has evolved over the years, and several methods have been developed to produce this important synthetic intermediate.
The choice of synthetic route depends on various factors such as the starting materials, the desired yield, and the cost of the reaction.
The use of microwave irradiation as a catalyst has recently been shown to be a highly efficient and cost-effective approach to synthesizing 6-aminoisoquinoline.