Abstract
The title compound, C19H15NO3, was synthesized by a Perkin reaction of 2-methyl-8-hy-droxy-quinoline and 4-formyl-2-methyl-benzoate in acetic anhydride under a nitro-gen atmosphere. The mol-ecule has an E conformation about the C=C bond, and the quinoline ring system and the benzene ring are inclined to one another by 29.22 (7)°. There is an intra-molecular O-H⋯N hydrogen bond in the 8-hy-droxy-quinoline moiety. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with an R22(28) ring motif. The dimers are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming sheets parallel to plane (10-1).
Highlights
2-methyl-8-hydroxyquinoline and 4-formyl-2-methylbenzoate in acetic anhydride under a nitrogen atmosphere
The dimers are linked by C—H O hydrogen bonds and C—H
8-hydroxyquinoline and its derivatives have played an important role in coordination chemistry (Albrecht et al, 2008; Cacciatore et al, 2013), shown to exhibit biological activity and have found various applications in the fields of synthetic chemistry (Song et al, 2006) and organic light-emitting diodes, which have been extensively exploited in the synthesis of luminescent metal complexes (Tang et al, 1987)
Summary
8-hydroxyquinoline and its derivatives have played an important role in coordination chemistry (Albrecht et al, 2008; Cacciatore et al, 2013), shown to exhibit biological activity (du Moulinet d’Hardemare et al, 2012) and have found various applications in the fields of synthetic chemistry (Song et al, 2006) and organic light-emitting diodes, which have been extensively exploited in the synthesis of luminescent metal complexes (Tang et al, 1987). It is highly desirable to develop new efficient 8-hydroxyquinoline derivatives for use in luminescent metal complexes. We report on the synthesis and crystal structure of a new. 8-hydroxyquinoline derivative, synthesized by the Perkin reaction of 2-methyl-8-hydroxyquinoline and 4-formyl-2methylbenzoate
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