Synthesis and structural characterization of 7-hydroxy-4-(naphthalen-2-yl)quinoline-2-carboxylic acid

This study examines a tandem heterocyclization of azines using carbonyl compounds and 3-aminophenol, which affords a potentially bioactive heterocycle. Condensation of equimolar amounts of 2-acetonaphthone with dibutyl oxalate in the presence of sodium, followed by treatment of the reaction mixture with acetic acid and subsequent addition of 3-aminophenol, enabled the preparative-scale synthesis of a new 7-hydroxy-4-(2′-naphthyl) quinoline-2-carboxylic acid. The structure of the isolated compound was confirmed by infrared spectroscopy, ¹H and ¹³C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Interpretation of the infrared spectrum revealed broadened, intense absorption bands attributable to the phenolic O–H group and the hydroxyl group of the carboxyl moiety, along with a characteristic C=O stretching band. The ¹H nuclear magnetic resonance spectrum recorded in deuterated dimethyl sulfoxide (DMSO-d₆) exhibited the expected multiplet, doublet, and singlet resonances of the aromatic protons. A downfield broadened singlet corresponded to the protons of the phenolic and carboxylic hydroxyl groups. The ¹³C nuclear magnetic resonance spectrum in deuterated dimethyl sulfoxide (DMSO-d₆) revealed downfield signals for the carboxyl carbon (COOH) and the C⁷–OH carbon. Electrospray ionization mass spectrometry (in acetonitrile containing a small amount of dimethyl sulfoxide) corroborated the proposed structure, showing the [M+H]⁺ and [M+Na]⁺ ions. The developed approach allows structurally diverse, potentially bioactive 4,7-disubstituted quinoline-2-carboxylic acids to be synthesized by varying the starting methyl ketones and nucleophiles.

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