4-Aminoquinoline

4-Aminoquinoline is a type of chemical compound that belongs to the class of quinolines. It is characterized by an amino group attached to the 4-position of the quinoline.

Structure and Properties

The structure of 4-aminoquinoline consists of a benzene ring fused to a pyridine ring, with an amino group attached at the 4-position. This gives the molecule a planar structure. The presence of the amino group increases the polarity of the molecule, which can affect its solubility in various solvents.

Synthesis

4-Aminoquinoline can be synthesized through the Skraup reaction, a method commonly used for the synthesis of quinolines. This involves the reaction of aniline with glycerol in the presence of sulfuric acid and an oxidizing agent.

Applications

4-Aminoquinoline is a key intermediate in the synthesis of various pharmaceutical drugs, including chloroquine and hydroxychloroquine, which are used in the treatment of malaria. It is also used in the synthesis of primaquine, an antimalarial drug that is effective against the liver stage of the malaria parasite.

Safety

As with many chemical compounds, care should be taken when handling 4-aminoquinoline. It can cause irritation to the skin and eyes, and may be harmful if swallowed or inhaled.

See Also

• Quinoline
• Chloroquine
• Hydroxychloroquine
• Primaquine