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Molecular Structure of Quinolin-1-(2-quinolyl)-2-one mesitylimine: An Unusual Amination Product of 2,4,6-Trimethylaniline and 2-Chloroquinoline

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Abstract

The molecular structure of quinolin-1-(2-quinolyl)-2-one mesitylimine has been determined. The Buchwald-Hartwig amination of mesitylaniline with two equivalents of 2-chloroquinoline results in dearomatization of one quinoline heterocycle, forming an imine with the mesitylaniline nitrogen and aminating the second 2-chloroquinoline via the cyclic nitrogen. The mesityl and quinoline moieties are nearly perpendicular to the plane of the central quinolyl structure. Rationalization of the imine formation is found by a consideration of the relative stability of the syn and anti conformations of the reaction intermediate. Crystal data: space group P21/c, a = 12.609(3), b = 15.010(3), c = 12.456(3) Å, β = 112.68(3)°; V = 2,175.3(8) Å3, Z = 4, R = 0.0649, wR2 = 0.1498.

Graphical Abstract

The amination of mesitylaniline with two equivalents of 2-chloroquinoline results in dearomatization of one quinoline heterocycle, forming an imine with the mesitylaniline nitrogen and aminating the second 2-chloroquinoline via the cyclic nitrogen.

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Acknowledgments

Financial support for this work is provided by Trans Ionics Corporation. The Robert A. Welch Foundation is acknowledged for funding of the Texas Center for Crystallography at Rice University. We acknowledge Dr. Robert C. Schucker and Michael F. Lynch for useful discussion.

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  1. Department of Chemistry, Rice University, 6100 Main Street, Houston, TX, 77005, USA

    John J. Allen, Christopher E. Hamilton & Andrew R. Barron

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  1. John J. Allen
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  2. Christopher E. Hamilton
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  3. Andrew R. Barron
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Correspondence to Andrew R. Barron.

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Allen, J.J., Hamilton, C.E. & Barron, A.R. Molecular Structure of Quinolin-1-(2-quinolyl)-2-one mesitylimine: An Unusual Amination Product of 2,4,6-Trimethylaniline and 2-Chloroquinoline. J Chem Crystallogr 38, 873–877 (2008). https://doi.org/10.1007/s10870-008-9455-2

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  • DOI: https://doi.org/10.1007/s10870-008-9455-2

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