Ethyl 5-aminopyridine-3-carboxylate
[CAS# 17285-76-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Aminopyridine
• Name: Ethyl 5-aminopyridine-3-carboxylate
• Synonyms: 5-Amino-3-pyridinecarboxylicacidethylester; 5-Amino-nicotinic acid ethyl ester; 5-Aminopyridine-3-carboxylic acid ethyl ester
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• CAS Registry Number: 17285-76-6
• SMILES: CCOC(=O)C1=CC(=CN=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.559, Calc.^*
• Boiling Point: 328.1±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 152.2±22.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

Ethyl 5-aminopyridine-3-carboxylate is an organic compound belonging to the class of aminopyridine derivatives. It has the molecular formula C₈H₁₀N₂O₂ and consists of a pyridine ring substituted with an amino group at the 5-position and an ethyl ester group at the 3-position. The compound is structurally related to various substituted pyridines that are widely used as intermediates in synthetic organic chemistry and pharmaceutical research.

The compound has been synthesized and studied in the context of heterocyclic chemistry. Its preparation typically involves the esterification of the corresponding 5-aminopyridine-3-carboxylic acid, a known compound in pyridine derivative research. Esterification reactions are carried out using ethanol in the presence of acidic catalysts or by other classical ester synthesis methods such as Fischer esterification. These reactions are well-documented and provide a reliable route to the ethyl ester form.

Ethyl 5-aminopyridine-3-carboxylate has been investigated as an intermediate in the synthesis of biologically active molecules. The amino group on the pyridine ring provides a site for further functionalization, including acylation, sulfonation, or coupling reactions with other heterocycles. Its carboxylate ester moiety can be hydrolyzed to regenerate the free acid, which is also useful in synthetic pathways. These features make the compound valuable in the stepwise construction of more complex chemical entities.

Several research studies have utilized this compound in the development of inhibitors targeting enzymes that interact with pyridine-based ligands. Derivatives of ethyl 5-aminopyridine-3-carboxylate have been explored for potential applications in medicinal chemistry, particularly in relation to antimicrobial and anti-inflammatory activities. However, the compound itself is not recognized as an active pharmaceutical ingredient and is instead employed primarily as a synthetic building block in the preparation of analogues for biological screening.

In dye chemistry and materials science, substituted pyridines including compounds like ethyl 5-aminopyridine-3-carboxylate have been used as precursors for the synthesis of ligands and coordination complexes. The ability of the pyridine nitrogen to coordinate with transition metals is well-established, and the presence of additional functional groups enhances the compound's coordination versatility. Such metal complexes have been studied for their optical properties or as catalysts in organic transformations.

Analytically, the compound may also be used as a reference standard or a model compound in chromatographic or spectroscopic studies. Its ultraviolet-visible (UV-Vis) absorption properties are typical of substituted pyridines and can be useful in method development or compound characterization.

While the industrial-scale application of ethyl 5-aminopyridine-3-carboxylate is limited, it remains an important compound in chemical synthesis and research. Its role as a key intermediate contributes to the exploration of new compounds in the pharmaceutical and materials sectors. The documented chemical transformations and synthetic routes involving this compound provide a foundation for its use in multiple domains of organic and medicinal chemistry.

Research publications and chemical databases have reported various reactions and synthetic protocols involving ethyl 5-aminopyridine-3-carboxylate, verifying its reproducibility and utility in laboratory settings. The compound is commercially available from specialized chemical suppliers and is utilized primarily in academic and industrial research focused on heterocyclic compound synthesis.

References

2023. Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes. RSC Adv., 13(20).
DOI: 10.1039/D3RA01778H

2021. Highly efficient on-DNA amide couplings promoted by micelle forming surfactants for the synthesis of DNA encoded libraries. Chem. Sci., 12(27).
DOI: 10.1039/D1SC03007H

1986. Synthesis and psychopharmacological and antihypoxic activity of some β-substituted pyridinecarboxylic acids. Pharmaceutical Chemistry Journal, 20(1).
DOI: 10.1007/bf00766873