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Preparation of 8-hydroxydecahydroquinoline

I. Ježo, M. Karvaš, and K. Tihlárik

Slovak Academy of Sciences, Bratislava


Abstract: Catalytic hydrogenation of 8-hydroxyquinoline (I) in glacial AcOH (PtO2) at 40° gave 8-hydroxy-1,2,3,4-tetrahydroquinoline (II), m. 115°; HCl salt m. 212°(cor.) (EtOH); O,N-di-Bz deriv. m. 136.5-7.5° (cor.) (50% EtOH), tests for phenolic OH group and >NH group pos. II was different in physicochem. consts. and compn. from the product prepd. by Fujise (CA 22, 3890). 8-Hydroxydecahydroquinoline (III) was prepd. by catalytic hydrogenation of the chloroplatinate (IV) of I in water suspension (Pd-C); III.HCl m. 255-6° (EtOH); III b12 123-4°, test for phenolic OH group neg., for >NH group pos. Catalytic hydrogenation of I in abs. MeOH (Raney Ni at 140-50° and 120 atm.) gave 1-methyl-8-hydroxydecahydroquinoline, b11 129-30°; picrate m. 183-4° (benzene); methiodide m. 280-1° (EtOH).

Full paper in Portable Document Format: 143a182.pdf (in Slovak)


Chemical Papers 14 (3) 182–186 (1960)

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