Ethyl 2-aminoisonicotinate
[CAS# 13362-30-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Ethyl 2-aminoisonicotinate
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• CAS Registry Number: 13362-30-6
• EC Number: 689-078-0
• SMILES: CCOC(=O)C1=CC(=NC=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.559, Calc.^*
• Boiling Point: 307.2±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 139.6±22.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Ethyl 2-aminoisonicotinate is an organic compound derived from isonicotinic acid, with the molecular formula C₈H₁₀N₂O₂. It consists of a pyridine ring substituted with an amino group at the 2-position and an ethyl ester group at the 4-position. The compound belongs to the class of aminopyridinecarboxylate esters and appears as a solid that is soluble in organic solvents such as ethanol, methanol, and dichloromethane. It is used as a versatile intermediate in the synthesis of a range of chemical and pharmaceutical substances.

The synthesis of ethyl 2-aminoisonicotinate has been well documented in chemical literature. A commonly used method begins with the nitration of ethyl isonicotinate, yielding ethyl 2-nitroisonicotinate, which is then subjected to catalytic hydrogenation or reduction using agents such as iron and hydrochloric acid or tin(II) chloride. This reaction selectively reduces the nitro group to an amino group, producing ethyl 2-aminoisonicotinate in good yields. The compound can also be synthesized by direct amination of halogenated ethyl isonicotinate derivatives under appropriate conditions.

Ethyl 2-aminoisonicotinate is primarily used as a building block in medicinal chemistry and drug discovery. The presence of both the amino group and the ester moiety enables a broad range of chemical transformations. The amino group is reactive towards acylation, sulfonation, and diazotization reactions, while the ester group is amenable to hydrolysis, amidation, and transesterification. These reactions allow chemists to incorporate the ethyl 2-aminoisonicotinate scaffold into more complex heterocyclic or peptidomimetic structures.

The compound serves as a precursor for the synthesis of substituted pyridines and fused-ring systems of pharmacological interest. Its derivatives have been investigated for their antibacterial, antifungal, anti-inflammatory, and anticancer properties. The compound has also been employed in the development of enzyme inhibitors and ligands for various biological targets. In several cases, ethyl 2-aminoisonicotinate has been used as an intermediate in the preparation of experimental drugs or bioactive molecules undergoing pharmacological screening.

In coordination and organometallic chemistry, the nitrogen atoms of ethyl 2-aminoisonicotinate provide donor sites for metal binding, allowing the formation of stable coordination complexes with transition metals. Such complexes are studied for their potential use in catalysis, as well as for their electronic and magnetic properties. The coordination behavior of this compound has been explored in relation to metal ions such as copper(II), nickel(II), and cobalt(II), and the resulting complexes have been characterized by various analytical methods.

Ethyl 2-aminoisonicotinate is also used in agricultural chemistry as an intermediate in the synthesis of compounds with herbicidal and fungicidal activity. Some of its derivatives have been examined for potential application in crop protection formulations due to their favorable physicochemical properties and biological activity profiles.

The compound is characterized by standard spectroscopic techniques including nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, and mass spectrometry (MS). The IR spectrum typically shows bands corresponding to N–H stretching vibrations from the amino group, C=O stretching from the ester group, and characteristic pyridine ring vibrations. NMR spectra reveal the substitution pattern of the pyridine ring and confirm the presence of the ethyl ester moiety.

Ethyl 2-aminoisonicotinate is a stable compound under normal conditions and should be stored in a dry, cool environment, protected from light. It is handled according to general laboratory safety practices, including the use of gloves, lab coats, and eye protection. Its reactivity and role in synthesis make it an important compound in academic research and industrial applications in the field of organic and medicinal chemistry.

References

2022. Diacylhydrazine Derivatives of 2-(5-(Pyridin-3-yl)-2H-Tetrazol-2-yl)Acetohydrazide and 2-(5-(Pyridin-4-yl)-2H-Tetrazol-2-yl)Acetohydrazide as Potential Inhibitors of Nucleotide Pyrophosphatase. Russian Journal of Bioorganic Chemistry, 48(5).
DOI: 10.1134/s1068162022050053

2018. Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs. Med. Chem. Commun., 9(6).
DOI: 10.1039/C8MD00139A

2012. One-Pot Three-Component Synthesis of 3-nitro-2-arylimidazo[1,2-a]pyridine Derivatives Using Air as an Oxidant. Chemistry - An Asian Journal, 7(8).
DOI: 10.1002/asia.201200319