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6-Isoquinolinecarbonitrile(9CI) is an important organic compound that is widely used in various industries, including the chemical industry.
It is a synthetic chemical that is commonly used as a building block for the synthesis of other chemicals and materials.
The synthetic routes of 6-Isoquinolinecarbonitrile(9CI) can be broadly classified into two categories: classical synthetic routes and modern synthetic routes.
Classical Synthetic Routes of 6-Isoquinolinecarbonitrile(9CI)
The classical synthetic routes of 6-Isoquinolinecarbonitrile(9CI) involve the use of traditional synthesis methods that have been in use for many years.
One of the classical synthetic routes involves the reaction of anthranilic acid with sodium hydroxide to form anthranilic sodium sulfate.
This intermediate is then heated with a mixture of sodium hydroxide and ammonia to form 6-Isoquinoline-N-oxide, which is subsequently reduced with hydrogen in the presence of a noble metal catalyst, such as Pt/C, to form 6-Isoquinolinecarbonitrile(9CI).
Another classical synthetic route involves the reaction of 2-chloroacetophenone with urea in the presence of an acid catalyst, such as sulfuric acid, to form 2-aminocyclohexanecarboxylic acid.
This intermediate is then treated with hydrogen cyanide and sodium hydroxide to form 6-Isoquinoline-N-oxide, which is subsequently reduced with hydrogen in the presence of a noble metal catalyst, such as Pt/C, to form 6-Isoquinolinecarbonitrile(9CI).
Modern Synthetic Routes of 6-Isoquinolinecarbonitrile(9CI)
The modern synthetic routes of 6-Isoquinolinecarbonitrile(9CI) involve the use of more efficient and sustainable synthesis methods that have been developed in recent years.
One of the most popular modern synthetic routes involves the reaction of aniline with hydrogen cyanide in the presence of a Lewis acid catalyst, such as aluminum chloride, to form N-phenylmaleimide.
This intermediate is then treated with ammonia and a solvent, such as DMF or DMA, to form 6-Isoquinoline-N-oxide, which is subsequently reduced with hydrogen in the presence of a noble metal catalyst, such as Pt/C, to form 6-Isoquinolinecarbonitrile(9CI).
Another modern synthetic route involves the reaction of 4-chloroaniline with 4-aminotoluene in the presence of a phase transfer catalyst, such as tetrabutylammonium iodide, and a solvent, such as THF or DMF, to form 3-chloro-4-(4-aminotoluene)aniline.
This intermediate is then treated with sodium hydroxide and hydrogen cyanide to form 6-Isoquinoline-N-oxide, which is subsequently reduced with hydrogen in the presence of a noble metal catalyst, such as Pt/C, to form 6-Isoquinolinecarbonitrile(9CI).
Advantages of the Synthetic Routes of 6-Isoquinolinecarbonitrile(9CI)
The synthetic routes of 6-Isoquinolinecarbonitrile(9CI) offer several advantages to the chemical industry.
One of the primary advantages is the availability of the starting materials, which are easily accessible and relatively inexpensive.
Additionally, the synthetic routes of