7-chloro-4-hydroxyquinoline

7-Chloro-4-hydroxyquinoline is a chemical compound that belongs to the class of quinoline derivatives. It is characterized by the presence of a chlorine atom at the 7th position and a hydroxyl group at the 4th position on the quinoline ring. This compound is of interest in medicinal chemistry due to its potential biological activities and its role as an intermediate in the synthesis of various pharmacologically active agents.

Chemical Structure and Properties

7-Chloro-4-hydroxyquinoline has the molecular formula C₉H₆ClNO. The quinoline ring system is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. The presence of the chlorine atom and the hydroxyl group influences the electronic properties and reactivity of the compound.

Physical Properties

• Molecular Weight: 179.60 g/mol
• Appearance: Typically a crystalline solid
• Melting Point: Approximately 200-205 °C
• Solubility: Soluble in organic solvents such as ethanol and dimethyl sulfoxide (DMSO)

Synthesis

The synthesis of 7-chloro-4-hydroxyquinoline can be achieved through various methods, often involving the chlorination of 4-hydroxyquinoline. One common approach is the reaction of 4-hydroxyquinoline with a chlorinating agent such as phosphorus oxychloride (POCl₃) or thionyl chloride (SOCl₂), followed by purification steps to isolate the desired product.

Applications in Medicinal Chemistry

7-Chloro-4-hydroxyquinoline serves as a key intermediate in the synthesis of several antimalarial and antibacterial agents. Its derivatives have been studied for their potential to inhibit the growth of Plasmodium falciparum, the parasite responsible for malaria, as well as various bacterial strains.

Derivatives and Related Compounds

• Chloroquine: A well-known antimalarial drug that is structurally related to 7-chloro-4-hydroxyquinoline.
• Hydroxychloroquine: Another antimalarial drug with similar structural features.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 7-chloro-4-hydroxyquinoline. It should be stored in a cool, dry place, and protective equipment such as gloves and goggles should be worn to prevent skin and eye contact.

Also see

• Quinoline
• Chloroquine
• Hydroxychloroquine
• Antimalarial drugs