European Journal of Chemistry

Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide

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Fares Hezam Al-Ostoot
Jigmat Stondus
Sumati Anthal
Geetha Doddenahally Venkatesh
Yasser Hussein Eissa Mohammed
Mandayam Anandalwar Sridhar
Shaukath Ara Khanum
Rajni Kant

Abstract

Medicinal chemistry of indole analogs constitutes important therapeutic agents with anti-oxidant, anti-HIV and anti-cancer activities. Indole nucleus is frequently found in synthetic and natural products, pharmaceuticals, functional materials, agrochemicals, etc. The title compound, N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide (5), has been synthesized in good yield by stirring the compound N-(2-aminophenyl)-2-(4-chlorophenoxy)acetamide (3) with 1H-indole-2-carboxylic acid (4), in dry dichloromethane followed by the addition of 2,6-lutidine, and o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl uraniumtetrafluoroborate in cooled condition. Compound 5 was synthesized and characterized by the conventional spectroscopic techniques (1H NMR, 13C NMR and LC-MS) and the three-dimensional structure was elucidated by using single crystal X-ray diffraction methods. It crystallizes in the monoclinic crystal system with space group P21/c. The structure was solved by direct methods and refined by full matrix least square procedure to a final R value of 0.043 for 2490 observed reflections. Three intra-molecular interactions of the type N-H···N and C-H···N were observed. The packing of molecules in the unit cell is governed by N-H···O and C-H···O intermolecular H-boned interactions which leads to the formation of infinite staking chain along [001] direction. In addition, two weak C-H···π interactions also contribute to molecular packing.


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Al-Ostoot, F. H.; Stondus, J.; Anthal, S.; Venkatesh, G. D.; Mohammed, Y. H. E.; Sridhar, M. A.; Khanum, S. A.; Kant, R. Synthesis, Spectroscopic and X-Ray Crystallographic Analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-Indole-2-Carboxamide. Eur. J. Chem. 2019, 10, 234-238.

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Department of Science and Technology (Project No, EMR/2014/000467), India.
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