3-AMINO-2-CHLORO-ISONICOTINIC ACID METHYLESTER Manufacturer CAS No.: 173435-41-1

What is 3-Amino-2-Chloro-Isonicotinic Acid Methyl Ester ?

3-Amino-2-Chloro-Isonicotinic Acid Methyl Ester Cas No.: 173435-41-1 is an organic compound characterized by a substituted pyridine ring with functional groups that include an amino group, a chlorine atom, and a methyl ester.

Chemical Structure and Properties

• Chemical Formula: C7H7ClN2O2
• IUPAC Name: Methyl 3-amino-2-chloropyridine-4-carboxylate
• Molecular Structure:
  • Pyridine Ring: A six-membered aromatic ring with one nitrogen atom.
  • Substituents:
    • 3-Amino Group: An -NH₂ group attached to the third carbon of the pyridine ring.
    • 2-Chloro Group: A chlorine atom attached to the second carbon of the pyridine ring.
    • Methyl Ester Group: A -COOCH₃ group attached to the fourth carbon of the pyridine ring, derived from the esterification of carboxylic acid.

The presence of these substituents significantly influences the chemical reactivity and biological activity of the compound.

Main Application

1. Pharmaceutical Industry:
   • Intermediate in Drug Synthesis: Researchers use this compound as an intermediate in the synthesis of pharmaceuticals. Its functional groups make it a versatile building block for constructing more complex bioactive molecules.
   • Antiviral and Antibacterial Agents: Researchers have explored compounds derived from substituted isonicotinic acids, like 3-amino-2-chloro-isonicotinic acid methyl ester for their potential as antiviral and antibacterial agents. The modifications on the pyridine ring can enhance the interaction with biological targets.
2. Development of Anti-Tuberculosis Drugs:
   • Isoniazid Derivatives: Isonicotinic acid derivatives are critical in the synthesis of anti-tuberculosis drugs such as isoniazid. The amino and ester functionalities allow for further chemical transformations that lead to potent drugs targeting Mycobacterium tuberculosis.
   • Drug Candidate Screening:  part of drug discovery programs aimed at finding new treatments for tuberculosis by modifying the pyridine scaffold.
3. Chemical Research:
   • Heterocyclic Chemistry: It serves as an important starting material in the study and synthesis of heterocyclic compounds, which are fundamental in medicinal chemistry for developing new therapeutic agents.
   • Synthesis of Complex Molecules: The compound’s unique combination of functional groups makes it suitable for use in multi-step synthetic processes to create complex molecules for various applications.
4. Agrochemicals:
   • Herbicide and Pesticide Synthesis: Researchers use similar pyridine derivatives in the synthesis of herbicides and pesticides. The 3-amino and 2-chloro substituents can enhance the biological activity against pests and weeds.
   • Plant Growth Regulators: Pyridine derivatives also find use in developing plant growth regulators that help in managing crop growth and improving yield.