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Title

A Probe into Hydrolysis of Nitrile Moiety in 2-Amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Year: 1400
COI: JR_CHM-5-1_008
Language: EnglishView: 96
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Authors

Samira Basafa - Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
Abolghasem Davoodnia - Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
S. Ali Beyramabadi - Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
Mehdi Pordel - Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

Abstract:

2-Amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carbonitrile 2 was prepared by the reaction of N-methylisatoic anhydride 1 with malononitrile via the ring-opening/ring closure pathway. The treatment of this compound with concentrated sulfuric acid at 100 °C gave a mixture of 2-amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 3 and 2-amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 4. The NMR analysis showed that the ratio of compound 3 to 4 in the mixture was one to two (1:2). When the later reactionwas performed in the presence of NaOH in refluxing H2O:EtOH, the compounds 3 and 4 were not formed, but instead, ring cleavage occurred to give compound 2-(methylamino) benzoic acid 5 in high yield. Density functional theory (DFT) calculations at the M06-2X/6-311+G(d,p) level of theory was also used to compute the 1H NMR chemical shifts of the compounds 3 and 4. Good agreement between the DFT-calculated 1H NMR chemical shifts and corresponding experimental values confirmed the suitability of the optimized geometries for these compounds. Characteristics of the bonding interactions were explored using the atoms in molecules (AIM) analysis.

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This Paper COI Code is JR_CHM-5-1_008. Also You can use the following address to link to this article. This link is permanent and is used as an article registration confirmation in the Civilica reference:

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Basafa, Samira and Davoodnia, Abolghasem and Beyramabadi, S. Ali and Pordel, Mehdi,1400,A Probe into Hydrolysis of Nitrile Moiety in 2-Amino-1-methyl-4-oxo-1,4-dihydroquinoline-3-carbonitrile,https://civilica.com/doc/1141810

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