Production Method 1

110443-51-1

958332-94-0

958332-97-3

Reaction Conditions

1.1 Reagents: Phosphoric tribromide Solvents: Dichloromethane ;  1 h, 50 °C; 50 °C → 0 °C
1.2 Reagents: Ammonium hydroxide Solvents: Water ;  3 h, cooled

Reference

Preparation of bicyclic amide derivatives as ion-channel ligands

, World Intellectual Property Organization, , ,

Ethyl 2-bromoquinoline-6-carboxylate Raw materials

• 6-Quinolinecarboxylic acid, ethyl ester, 1-oxide

Ethyl 2-bromoquinoline-6-carboxylate Preparation Products

• Ethyl 2-bromoquinoline-6-carboxylate (958332-94-0)
• Ethyl 4-bromoquinoline-6-carboxylate (958332-97-3)

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Ethyl 2-bromoquinoline-6-carboxylate (CAS No. 958332-94-0): An Overview of Its Synthesis, Properties, and Applications

Ethyl 2-bromoquinoline-6-carboxylate (CAS No. 958332-94-0) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique molecular structure, offers a wide range of applications, particularly in the development of novel therapeutic agents and as an intermediate in synthetic pathways.

The synthesis of Ethyl 2-bromoquinoline-6-carboxylate involves a series of well-defined chemical reactions. One common approach is the bromination of quinoline followed by esterification. The initial step typically involves the bromination of 6-quinolinecarboxylic acid using a suitable brominating agent such as N-bromosuccinimide (NBS) or bromine in an appropriate solvent. The resulting 2-bromoquinoline-6-carboxylic acid is then subjected to esterification with ethanol in the presence of a catalyst like sulfuric acid or p-toluenesulfonic acid to yield the desired product.

The physical properties of Ethyl 2-bromoquinoline-6-carboxylate are crucial for its handling and application. It is a solid at room temperature with a melting point ranging from 105 to 107°C. The compound is slightly soluble in water but exhibits good solubility in organic solvents such as ethanol, methanol, and dichloromethane. These properties make it suitable for various synthetic processes and analytical techniques.

In terms of chemical properties, Ethyl 2-bromoquinoline-6-carboxylate is known for its reactivity and functional group versatility. The bromine atom at the 2-position can undergo various substitution reactions, making it a valuable intermediate in the synthesis of more complex molecules. Additionally, the ester group can be hydrolyzed to form the corresponding carboxylic acid or transformed into other functional groups through various chemical transformations.

Recent research has highlighted the potential of Ethyl 2-bromoquinoline-6-carboxylate in medicinal chemistry. Studies have shown that quinoline derivatives, including those with bromine substituents, exhibit promising biological activities such as antimicrobial, antiviral, and anticancer properties. For instance, a study published in the Journal of Medicinal Chemistry reported that certain quinoline derivatives with bromine substituents demonstrated significant antitumor activity against various cancer cell lines.

The pharmaceutical applications of Ethyl 2-bromoquinoline-6-carboxylate are diverse and expanding. It serves as an important intermediate in the synthesis of drugs targeting specific biological pathways. One notable example is its use in the development of inhibitors for kinases, enzymes that play critical roles in cellular signaling and disease progression. These inhibitors have shown promise in treating conditions such as cancer and inflammatory diseases.

Beyond its role as an intermediate, Ethyl 2-bromoquinoline-6-carboxylate itself has been explored for its potential therapeutic effects. Research has indicated that it may possess anti-inflammatory properties due to its ability to modulate key signaling pathways involved in inflammation. This makes it a potential candidate for further investigation as a lead compound in drug discovery efforts.

The safety and handling of Ethyl 2-bromoquinoline-6-carboxylate are important considerations for researchers and laboratory personnel. While it is not classified as a hazardous material, proper precautions should be taken to ensure safe handling and storage. It is recommended to handle the compound under well-ventilated conditions and to use appropriate personal protective equipment (PPE) such as gloves and safety goggles.

In conclusion, Ethyl 2-bromoquinoline-6-carboxylate (CAS No. 958332-94-0) is a valuable compound with significant potential in both synthetic chemistry and pharmaceutical research. Its unique structure and versatile reactivity make it an essential building block for the development of novel therapeutic agents and advanced materials. As research continues to uncover new applications and properties, this compound is likely to play an increasingly important role in advancing scientific knowledge and improving human health.

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