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6,7-Dihydro-5H-quinolin-8-one, also known as quinoline-8-carboxaldehyde, is a versatile organic compound that finds widespread use in various applications in the chemical industry.
The compound can be synthesized through several routes, each with its own advantages and disadvantages.
In this article, we will discuss some of the synthetic routes of 6,7-dihydro-5H-quinolin-8-one, their applications, and the advantages and disadvantages of each route.
- Synthesis via the Williamson ether synthesis
The Williamson ether synthesis is a popular synthetic route for the preparation of quinoline-8-carboxaldehyde.
In this route, the compound is synthesized by treating anthranilic acid with sodium hydroxide and then reacting the resulting anthranilic sodium salt with ether and acid.
The reaction is as follows:
Anthranilic acid + NaOH -> Anthranilic sodium salt
Anthranilic sodium salt + 2 equivalents of ether + H2SO4 -> 6,7-Dihydro-5H-quinolin-8-one
The Williamson ether synthesis is a relatively simple and cost-effective method for the synthesis of 6,7-dihydro-5H-quinolin-8-one.
It is also highly reproducible, and the product yield is generally high.
However, the reaction requires the use of corrosive reagents such as sulfuric acid, which can be potentially dangerous.
- Synthesis via the P2Pi synthesis
Another popular synthetic route for 6,7-dihydro-5H-quinolin-8-one is the P2Pi synthesis.
In this route, the compound is synthesized by treating 3-pyridinecarboxaldehyde with aqueous sodium hydroxide and then reacting the resulting 3-pyridinecarboxylic acid with potassium cyanide.
The reaction is as follows:
3-Pyridinecarboxaldehyde + NaOH -> 3-Pyridinecarboxylic acid
3-Pyridinecarboxylic acid + KCN -> 6,7-Dihydro-5H-quinolin-8-one
The P2Pi synthesis is another efficient method for the synthesis of 6,7-dihydro-5H-quinolin-8-one.
It is less hazardous than the Williamson ether synthesis, as it does not require the use of corrosive reagents.
The product yield is also generally high, and the reaction is highly reproducible.
- Synthesis via the nitrile oxide synthesis
The nitrile oxide synthesis is a versatile synthetic route for the preparation of quinoline-8-carboxaldehyde.
In this route, the compound is synthesized by treating quinoline-7-carboxaldehyde with nitrile oxide and then hydrolyzing the resulting nitrile to yield 6,7-dihydro-5H-quinolin-8-one.
The reaction is as follows:
Quinoline-7-carboxaldehyde + NO -> Quinoline-8-nitrile
H2O -> Quinoline-8-carboxaldehyde
The nitrile oxide synthesis is a useful method for the synthesis of 6,7-dihydro-5H-quinolin-8-one, as it allows for the conversion of a readily available starting material, quinoline-7-carboxaldehyde.
The reaction is highly efficient, and the product yield is generally high.
However, the reaction requires the use of nitrile oxide, which is an expensive and potentially hazardous reagent.
- Synthesis via the Wacker-type