1-[(2-Chloro-7-methyl-3-quinol­yl)meth­yl]pyridin-2(1H)-one

S Mohana Roopan; F Nawaz Khan; Atul Kumar Kushwaha; Venkatesha R Hathwar; Mehmet Akkurt

doi:10.1107/S1600536810011177

. 2010 Mar 27;66(Pt 4):o960. doi: 10.1107/S1600536810011177

1-[(2-Chloro-7-methyl-3-quinolyl)methyl]pyridin-2(1H)-one

S Mohana Roopan ^a, F Nawaz Khan ^a, Atul Kumar Kushwaha ^a, Venkatesha R Hathwar ^b, Mehmet Akkurt ^c,^*

PMCID: PMC2984016 PMID: 21580763

Abstract

In the title compound, C₁₆H₁₃ClN₂O, the quinoline ring system is essentially planar, with a maximum deviation of 0.021 (2) Å. The pyridone ring is oriented at a dihedral angle of 85.93 (6)° with respect to the quinoline ring system. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules along the b axis. Weak π–π stacking interactions [centroid–centroid distances = 3.7218 (9) and 3.6083 (9) Å] are also observed.

Related literature

For related structures, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For the synthesis of 2-pyridone derivatives, see: Conreaux et al. (2005 ▶); Roopan & Khan (2009 ▶); Roopan et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₃ClN₂O
M _r = 284.73
Monoclinic,
a = 11.8934 (3) Å
b = 11.1092 (3) Å
c = 21.2858 (6) Å
β = 102.413 (3)°
V = 2746.67 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.26 × 0.21 × 0.18 mm

Data collection

Oxford Xcalibur diffractometer with an Eos (Nova) CCD detector
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T _min = 0.932, T _max = 0.952
13638 measured reflections
2556 independent reflections
1893 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.095
S = 1.10
2556 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011177/is2533sup1.cif

e-66-0o960-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011177/is2533Isup2.hkl

e-66-0o960-Isup2.hkl^{(123.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.93	2.37	3.299 (2)	173

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the FIST program for the data collection at SSCU, IISc, Bangalore and Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

The pyridone analogues such as naturally occurring mappicine based molecule have been focused of great interest by reason of their diversified biological activities. N-alkylated 2-pyridones are important intermediates in the synthesis of alkaloids as illustrated by the recent synthetic approaches toward the mappicine family. Thus, modifications of biologically active mappicine synthons may lead to achieve the highly expected effective drugs (Roopan & Khan, 2009). Having succeeded in developing a practical, alternative synthesis of pyridine (Conreaux et al., 2005), we then focused our attention on the general applicability of the N-alkylation (Roopan et al., 2010) of pyridones by mean of the t-BuOK/THF system In connection with the program of synthesis of 2-pyridone analogues, we report herein the synthesis of 1-[(2-chloro-7-methylquinolin-3yl)-methyl]-pyridine-2(1H)-one.

In the title molecule, the quinoline ring system (N1/C1–C9) is almost planar, with maximum deviations of 0.021 (1) Å for N1 and -0.021 (2) Å for C7 (Fig. 1). The pyridone ring (N2/C11—C15) is oriented at a dihedral angle of 85.93 (6)° with respect to the quinoline ring system. In the crystal structure, intermolecular C—H···O hydrogen bonds contribute to the stability of the structure, linking the molecules along the [010] direction (Table 1 and Fig. 2). Weak π–π stacking interactions are also observed [Cg1···Cg3(3/2-x, 1/2-y, -z) = 3.7218 (9), where Cg1 and Cg3 are the centroids of the N1/C1–C3/C8/C9 and C4–C9 rings, respectively; Cg2···Cg2(2-x, y, 1/2-z) = 3.6083 (9) Å, where Cg2 is a centroid of the N2/C11–C15 ring].

Experimental

To a mixed well solution of 2-pyridone (95 mg, 1 mmol, in 2 ml of DMF), KO^tBu (112 mg, 1 mmol, in 10 ml THF) and 2-chloro-3-(chloromethyl)-7-methylquinoline (226 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, dried and purified by column chromatography using hexane and ethylacetate as the eluant. Crystals of suitable quality were grown by solvent evaporation from a diethylether solution.