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Updated: Aug 22, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Methyl 2-(3-chloro-2-methyl-anilino)pyridine-3-carboxyl-ate
1School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, Hubei 430205, People's Republic of China.
Abstract:
The title compound, C14H13ClN2O2, was obtained during an attempt to grow single crystals of 4-acetyl-phenyl 2-[(3-chloro-2-methyl-phen-yl)amino]-nicotinate in methanol, and was probably generated by alcoholysis. Two intra-molecular hydrogen bonds are formed, one between the N-H group and the carbonyl O atom of the ester and the other between the ortho sp 2CH group of the benzene ring and the pyridine N atom. Aromatic π-π stacking [shortest centroid-centroid separation = 3.598 (2) Å] is observed in the extended structure.
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