2-[(3-Chloro-2-methyl-phen-yl)amino]-quinoline-3-carb-oxy-lic acid
1School of Chemical Engineering and Pharmacy Wuhan Institute of Technology,Wuhan Hubei 430205 People's Republic of China.
Iucrdata
|July 6, 2026
Summary
A novel fenamic acid analogue was synthesized using palladium-catalyzed cross-coupling. The resulting molecule exhibits a near-planar structure and forms dimers through hydrogen bonding, offering insights into non-steroidal anti-inflammatory drug design.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Crystallography
Background:
- Fenamic acid derivatives are non-steroidal anti-inflammatory drugs (NSAIDs) with established therapeutic uses.
- Developing novel NSAIDs with improved properties or unique structural features is an ongoing area of research.
Purpose of the Study:
- To synthesize a novel fenamic acid analogue with a quinoline core.
- To characterize the synthesized compound's structure and intermolecular interactions.
Main Methods:
- Palladium-catalyzed Buchwald-Hartwig cross-coupling reaction between 2-chloro-quinoline-3-carboxylic acid and 3-chloro-2-methyl-aniline.
- Esterification and subsequent alkaline hydrolysis to yield the target carboxylic acid.
- X-ray crystallography to determine the molecular and crystal structure.
Main Results:
- Successful synthesis of the target compound, C17H13ClN2O2, an analogue of fenamic acid NSAIDs.
- The molecule displays a nearly planar conformation with a small dihedral angle (7.17°) between the quinoline and phenyl rings.
- Adjacent molecules form centrosymmetric carboxylic acid dimers stabilized by O-H⋯O hydrogen bonds.
Conclusions:
- The study presents a novel synthetic route to a fenamic acid analogue incorporating a quinoline moiety.
- The structural analysis reveals a near-planar conformation and characteristic hydrogen-bonded dimer formation, relevant for understanding drug-receptor interactions.
- This compound serves as a potential scaffold for further development in the field of anti-inflammatory agents.
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