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15.4.1 Product Subclass 1: Quinolin-2(1H)-ones

DOI: 10.1055/sos-SD-015-00917

Larsen, R. D.Science of Synthesis, (200515551.

One of the first syntheses of a compound of the quinoline class was that of quinolin-2-one, reported in 1852. The product was prepared by reductive cyclization of 2-nitrocinnamic acid [(2E)-3-(2-nitrophenyl)acrylic acid], a method that is still commonly used.[‌1‌] The quinolin-2-ones [quinolin-2(1H)-ones] are also commonly referred to as carbostyrils, 2-hydroxyquinolines, 2-quinolinols, or 2-oxoquinolines. Quinolin-2-ones have two tautomeric forms, the lactam form 1 and the phenolic form 2 (Scheme 1).[‌19‌] In the solid state, the compound exists predominately as the lactam 1.[‌20‌,‌21‌] The IR spectra of quinolin-2-ones in solution are generally difficult to obtain because of their low solubility in most IR spectroscopy solvents; however, by using a mixture of chloroform and dimethyl sulfoxide, good solubility has been achieved and quite intense amide carbonyl bands were observed, indicating that the amide tautomer predominates.[‌22‌] Other studies have also indicated that the amide form predominates.[‌23‌] Comparison of the UV spectra of quinolin-2-one, 2-methoxyquinoline, and 1-methylquinolinone confirmed that the lactam form 1 indeed predominates in solution.[‌4‌]

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