1-[(2-Chloro-8-methyl­quinolin-3-yl)­meth­yl]pyridin-2(1H)-one

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

doi:10.1107/S1600536810012730

. 2010 Apr 10;66(Pt 5):o1049. doi: 10.1107/S1600536810012730

1-[(2-Chloro-8-methylquinolin-3-yl)methyl]pyridin-2(1H)-one

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

PMCID: PMC2979145 PMID: 21579109

Abstract

In the title compound, C₁₆H₁₃ClN₂O, the quinoline ring system is approximately planar [maximum deviation 0.021 (2) Å] and forms a dihedral angle of 85.93 (6)° with the pyridone ring. Intermolecular C—H⋯O hydrogen bonding, together with weak C—H⋯π and π–π interactions [centroid-to-centroid distances 3.5533 (9) and 3.7793 (9) Å], characterize the crystal structure.

Related literature

For 2-pyridone analogues, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For the synthesis of 2-pyridone derivatives, see: Banerjee & Sereda (2009 ▶); Roopan & Khan (2009 ▶); Roopan et al. (2010 ▶); Dandepally & Williams (2009 ▶).

Experimental

Crystal data

C₁₆H₁₃ClN₂O
M _r = 284.73
Monoclinic,
a = 10.1513 (2) Å
b = 9.3917 (2) Å
c = 14.1430 (2) Å
β = 90.948 (2)°
V = 1348.17 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.931, T _max = 0.946
17649 measured reflections
2511 independent reflections
2088 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.100
S = 1.10
2511 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (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/S1600536810012730/im2191sup1.cif

e-66-o1049-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012730/im2191Isup2.hkl

e-66-o1049-Isup2.hkl^{(120.8KB, hkl)}

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

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

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.54	3.286 (2)	137
C6—H6⋯Cg1ⁱⁱ	0.93	2.61	3.4457 (18)	150

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the FIST programme for the data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. We also thank 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

As part of our search for new quinoline analogues, we focused on N-alkylation of 2-pyridinone using 2-chloro-3-(chloromethyl)-8-methylquinoline. N-alkylations are used in the synthesis of various heterocyclic (Dandepally & Williams, 2009) naturally occurring alkaloids. The chemistry of N-alkylation has received much attention due to their usefulness as building blocks in organic synthesis (Roopan et al., 2010). Compounds found in nature display a wide range of diversity in terms of their structures and physical and biological properties. The synthesis of privileged medicinal scaffolds is highly important as these compounds often act as a platform for developing pharmaceutical agents for diverse applications (Roopan & Khan, 2009). These vast applications have inspired the development of a number of methods for the preparation of pyridine nucleus (Banerjee & Sereda, 2009). However, literature studies reveal that most of the methods involve low isolated yields and long reaction times. On the basis of the interesting structures and biological activities exhibited by several heterocyclic systems possessing quinoline and pyridinone nuclei, we have synthesized a quinoline coupled pyridinone, i.e. 1-[(2-chloro-8-methylquinolin-3yl)-methyl]-pyridine-2(1H)-one.

The quinoline ring system (N1/C1–C3/C8/C9) of the title molecule in Fig. 1 is approximately planar, with maximum deviations of 0.021 (2) Å for C7, -0.021 (1) Å for N1 and 0.018 (2) Å for C5. It makes a dihedral angle of 85.93 (6)° with the pyridinone ring (N2/C11–C15). Intramolecular C—H···N, intermolecular C—H···O hydrogen bonding, together with weak C—H···π (Table 1) and π–π interactions [Cg1···Cg2(-x, 1/2 + y, 1/2 - z) = 3.5533 (9) Å and Cg2···Cg3(-x, -1/2 + y, 1/2 - z) = 3.7793 (9) Å, where Cg1, Cg2 and Cg3 are the centroids of the N1/C1–C3/C8/C9, N2/C11–C15 and C4–C9 rings, respectively], characterize the crystal structure. Fig. 2 shows the hydrogen bonding in terms of a packing diagrams of the title compound.

Experimental

To a vigorously stirred solution of 2-pyridinone (95 mg, 1 mmol, in 2 ml DMF) KO^tBu (112 mg, 1 mmol, in 10 ml THF) and 2-chloro-3-(chloromethyl)-8-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 it was cooled to room temperature and the excess of solvent was removed under reduced pressure. Crushed ice was mixed with the residue producing a white solid that was filtered and dried. Purification was performed by column chromatography using hexane and ethyl acetate (1:9) as the eluant. Crystals of suitable quality were grown by solvent evaporation from a solution of the compound in dichloromethane at room temperature.