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Updated: May 24, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-[(4-Bromo-phen-yl)(morpholin-4-yl)-meth-yl]naphthalen-2-ol
1School of Pharmaceutical Sciences, Nanjing University of Chinese Medicine, Nanjing 210046, People's Republic of China.
Abstract:
The title compound, C(21)H(20)BrNO(2), was obtained via a one-pot synthesis from the reaction of 4-bromo-benzaldehyde, 2-naphthol and morpholine. In the asymmetric unit, there are four mol-ecules with similar structures. The morpholine ring adopts a chair conformation, and the hy-droxy group links with the morpholine via an intra-molecular O-H⋯N hydrogen bond. The bromo-phenyl ring is approximately perpendicular to the mean pane of the naphthalene system at dihedral angles of 76.7 (3), 81.4 (3), 79.7 (3) and 84.5 (3)° in the four independent mol-ecules. Weak C-H⋯O hydrogen bonds are observed in the crystal.
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