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Updated: May 13, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-{(Z)-[3-(1-Hy-droxy-eth-yl)anilino]methyl-idene}naphthalen-2(1H)-one
Peter N Horton1, Mehmet Akkurt, Shaaban K Mohamed
1School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ England, England.
Abstract:
In the title compound, C19H17NO2, the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5)°, while the torsion angle of the C-N-C-C bridging group is 179.24 (17)°. The methyl group of the 1-phenyl-ethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The mol-ecular conformation is stabil-ized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C-H⋯O inter-actions, forming a two-dimensional slab-like network parallel to the bc plane.
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