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7-Chloro-4-iodoquinoline is an organic compound commonly used in the pharmaceutical and chemical industries.
It has various applications in the synthesis of other chemicals and drugs.
The synthetic routes of 7-chloro-4-iodoquinoline have been extensively studied, and various methods have been developed to synthesize this compound.
In this article, we will discuss the synthetic routes of 7-chloro-4-iodoquinoline in detail.
Method 1: via N-Chlorosuccinimide
One of the most commonly used methods to synthesize 7-chloro-4-iodoquinoline involves the use of N-chlorosuccinimide as a reagent.
N-Chlorosuccinimide is a strong nitrating agent that can efficiently convert chloride ion to chlorine dioxide.
The reaction proceeds through the following steps:
- Treatment of 2-amino-5-iodophenol with N-chlorosuccinimide in the presence of a solvent such as acetonitrile or DMF leads to the formation of N-chlorosuccinimide active ester.
- The N-chlorosuccinimide active ester undergoes a condensation reaction with 4-iodoaniline, which provides the desired product 7-chloro-4-iodoquinoline.
This method offers several advantages, such as the formation of a stable active ester, ease of workup, and the ability to perform the reaction under mild conditions.
Method 2: via Pd/C
Another method to synthesize 7-chloro-4-iodoquinoline involves the use of palladium catalyst (Pd/C).
The reaction proceeds through the following steps:
- The reaction of 2-iodo-5-methylphenol with 4-bromoaniline in the presence of Pd/C and a solvent such as acetonitrile or DMF leads to the formation of 4-(4-iodophenyl)butyric acid.
- The formation of 4-(4-iodophenyl)butyric acid is followed by the treatment with hydrogen chloride in the presence of a solvent such as ethanol, which provides 7-chloro-4-iodoquinoline.
This method offers several advantages, such as the mild reaction conditions, ease of workup, and the ability to perform the reaction in one step.
Method 3: via Sodium Hypochlorite
A simple and cost-effective method to synthesize 7-chloro-4-iodoquinoline involves the use of sodium hypochlorite as a reagent.
The reaction proceeds through the following steps:
- The reaction of 2-amino-5-iodophenol with sodium hypochlorite in the presence of a solvent such as water or ethanol leads to the formation of 7-chloro-4-iodoquinoline.
This method is simple and easy to perform, but it requires careful handling of the reagents because sodium hypochlorite is highly corrosive.
In conclusion, 7-chloro-4-iodoquinoline is an important building block in the synthesis of other chemicals and drugs.
There are several methods available for its synthesis, and the choice of method depends on the specific requirements of the synthesis.
The three methods discussed in this article are commonly used in the industry, and they offer several advantages in terms of reaction conditions, ease of workup, and cost-effectiveness.