1-[(2-Chloro-7,8-dimethylquinolin-3-yl)methyl]pyridin-2(1H)-one

In the title compound, C17H15ClN2O, the quinoline ring system is nearly planar, with a maximum deviation from the mean plane of 0.074 (2) Å, and makes a dihedral angle of 81.03 (7)° with the pyridone ring. The crystal packing is stabilized by π–π stacking interactions between the pyridone and benzene rings of the quinoline ring system [centroid–centroid distance = 3.6754 (10) Å]. Furthermore, weak intermolecular C—H⋯O hydrogen bonding links molecules into supramolecular chains along [001].

In the title compound, C 17 H 15 ClN 2 O, the quinoline ring system is nearly planar, with a maximum deviation from the mean plane of 0.074 (2) Å , and makes a dihedral angle of 81.03 (7) with the pyridone ring. The crystal packing is stabilized bystacking interactions between the pyridone and benzene rings of the quinoline ring system [centroidcentroid distance = 3.6754 (10) Å ]. Furthermore, weak intermolecular C-HÁ Á ÁO hydrogen bonding links molecules into supramolecular chains along [001].   Table 1 Hydrogen-bond geometry (Å , ).  have attracted considerable interest because of their significant activity. Particularly, five and six membered heterocyclic compounds containing one or two hetero atoms fused to a quinoline ring are found in natural products. The search for new anticancer drugs from nature continues to be a fruitful activity, as evidenced by the successes of natural products as pharmaceutical agents. Nitrogen containing heterocyclic compounds, recognized pharmacophores has received great attention in drug discovery and lead optimization. The chemistry of N-alkylation has recently received much attention due to their usefulness as building blocks in organic synthesis (Roopan et al., 2010). On the basis of the interesting structures and biological activities exhibited by several heterocyclic systems possessing quinoline and pyridone nucleus, we have synthesized a quinoline coupled pyridone, i.e., 1-[(2-chloroquinolin-3yl)-methyl]-pyridine-2(1H)-one.

Experimental
To a mixed well solution of 2-pyridone (95 mg, 1 mmol, in 2 ml of DMF), KO t Bu (112 mg, 1 mmol in 10 ml of THF) and 2-chloro-3-(chloromethyl)-7,8-dimethylquinoline (240 mg, 1 mmol) were added and the resulting mixture was refluxed at 343 K for 1 h. After the completion of the reaction, cooled and removed the excess of solvent under reduced pressure.
Crushed ice was mixed with the residue. White solid was formed, filtered and dried, purified by column chromatography using hexane and ethylacetate as the eluant. Crystals of suitable quality were grown by solvent evaporation from a solution of the compound in chloroform.

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C-H = 0.93-0.97 Å and U iso (H) = 1.2 or 1.5U eq (C). Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and tor-

sion angles
Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted Rfactors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.