Research Article: 4-[2-(Benzyl­amino)­phen­yl]-2,6-dimethyl­quinoline N-oxide

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Mario Geffe, Dieter Schollmeyer, Heiner Detert.


The title compound, C24H22N2O, was obtained in a two-step procedure from the corresponding 4-(2-iodo­phen­yl)quinoline. The quinoline system is approximately planar [maximum deviation from the least-squares plane = 0.021 (2) Å]. The planes of the quinoline system and the phenyl ring subtend a dihedral angle of 78.08 (8)°. In the crystal, pairs of mol­ecules are connected via a center of symmetry and linked by a pair of angular N—H⋯O hydrogen bond. These dimers form columns oriented along the c axis.

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For aminations of iodo­lium salts, see: Letessier et al. (2011a ▶,b ▶), Letessier & Detert (2012 ▶). For quinoline N-oxides, see: Moreno-Fuquen et al. (2007 ▶); Ivashevskaja et al. (2002 ▶); Fahl­quist et al. (2006 ▶). For heteroanalogous carbazoles, see: Dassonneville et al. (2010 ▶, 2011 ▶); Nissen & Detert (2011 ▶). For Buchwald-Hartwig amination, see: Hartwig (1999 ▶); Muci & Buchwald (2002 ▶). For twist of o-substituted biaryls, see: Miao et al. (2009 ▶); Moschel et al. (2011 ▶).