In the title compound, C30H24Cl2N 2O3, the two quinoline ring systems are almost planar [maximum deviations = 0.029 (2) and 0.018 (3) Å] and the dihedral angle between them is 4.17 (8)°. The dihedral angle between the phenyl ring and its attached quinoline ring is 69.06 (13)°. The packing is stabilized by C - H⋯O, C - H⋯N, weak π-π stacking [centroid-centroid distances = 3.7985 (16) and 3.7662 (17) Å] and C - H⋯π inter-actions.

Mohana Roopan S

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Nawaz Khan F

Hathwar V.R

Akkurt M.

Fulltext

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

&nbsp;

&nbsp;

VIT University

Ethyl 6-chloro-2-[(2-chloro-7,8-dimethyl-quinolin-3-yl)meth-oxy]-4-phenyl-quinoline-3-carboxyl-ate.

Acta Crystallographica Section E Structure Reports Online

An efficient and regioselective O-alkylation of amides with a variety of electrophiles in the presence of silver nanoparticles is reported as part of our recent research on building blocks for synthesis of natural products. The nano-silver catalyst initiates O-alkylation of the amides by heteroalkyl halides. Reaction of equimolar 3-acetyl-6-chloro-4-phenylquinolin-2(1H)-one and 2-chloro-3-(chloro-methyl)quinolines in the presence of silver nanoparticles in DMSO solution under reflux condition leads to the formation of 1-{1-[2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones. © Springer Science+Business Media B.V. 2011.

Research on Chemical Intermediates

Regioselective O-alkylation: synthesis of 1-{2-[(2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones

The title compound, C18H16N2O, crystallizes in the triclinic space group P1, with four independent mol-ecules in the asymmetric unit wherein two mol-ecules have an irregular -ac, -ac, +ap conformation (ap, antiperiplanar; ac, anticlinal), while the other mol-ecules exhibit a different, +ac, +ac, +ap conformation. The planar (r.m.s. deviation = 0.006 Å in each of the four molecules) quinoline ring systems of the four mol-ecules are oriented at dihedral angles of 32.8 (2), 33.4 (2), 31.7 (2) and 32.3 (2)° with respect to the benzene rings. Intra-molecular N - H⋯N inter-actions occur in all four independent mol-ecules. The crystal packing is stabilized by inter-molecular N - H⋯O and C - H⋯O hydrogen bonds, and are further consolidated by C - H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.728 (3), 3.722 (3), 3.758 (3) and 3.705 (3) Å].

N-[2-(4-Methyl-2-quinolyl)phenyl]acetamide: aP1 structure withZ= 4

In the title mol-ecule, C28H20Cl2N 2O2, the dihedral angle between the 2-chloro-quinoline and 6-chloro-quinoline rings is 7.55 (6)°. The dihedral angle between the phenyl ring and its attached quinoline ring is 62.59 (4)°. In the crystal, aromatic π-π stacking inter-actions [centroid-centroid distances = 3.771 (3) and 3.612 (3) Å] help to establish the packing.

1-{6-Chloro-2-[(2-chloro-8-methyl-3-quinolyl)methoxy]-4-phenylquinolin-3-yl}ethanone

In the title compound, C28H20Cl2N 2O2, the 2-chloroquinoline and 6-chloroquinoline ring systems are twisted slightly, making a dihedral angle of 4.05 (3)°. The dihedral angle between the 2quinoline ring system and the phenyl ring attached to it is 74.43 (5)°. In the crystal structure, a pair of inter-molecular C-H⋯O hydrogen bonds connect the molecules, forming centrosymmetric dimers with R22(16) motifs. The dimers are further consolidated by a C-H⋯π inter-action and a π-π stacking inter-action with a centroid-centroid distance of 3.6562 (10) Å.

1-{6-Chloro-2-[(2-chloro-6-methylquinolin-3-yl)methoxy]-4-phenylquinolin-3-yl}ethanone

In the title compound, C27H18Cl2N 2O2, the 2-chloroquinoline and 6-chloroquinoline rings are almost planar, with maximum deviations from their mean planes of 0.072 (1) and 0.044 (1) Å, respectively, for the Cl atoms. The inter-planar angle between these rings is 14.36 (5)°. The inter-planar angle between the 6-chloroquinoline and phenyl rings is 66.00 (8)°. In the crystal, molecules are inter-linked by weak C-H⋯O, C-H⋯π and π-π stacking [centroid-centroid distances = 3.7453 (10) and 3.7557 (9) Å] inter-actions.

Journal	Acta Crystallographica Section E Structure Reports Online
Publisher	International Union of Crystallography (IUCr)
ISSN	16005368
Open Access	0