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.