rac-2-(2-Chloro-6-methyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one

Abdelmalek Bouraiou; Sofiane Bouacida; Carboni Bertrand; Thierry Roisnel; Ali Belfaitah

doi:10.1107/S1600536812020831

. 2012 May 12;68(Pt 6):o1701–o1702. doi: 10.1107/S1600536812020831

rac-2-(2-Chloro-6-methylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one

Abdelmalek Bouraiou ^a, Sofiane Bouacida ^b,^*, Carboni Bertrand ^c, Thierry Roisnel ^d, Ali Belfaitah ^a

PMCID: PMC3379295 PMID: 22719493

Abstract

In the title compound, C₁₉H₁₅ClN₂O, the quinoline ring forms a dihedral angle of 43.24 (1)° with the benzene ring of the dihydroquinolinyl system. In the crystal, molecules are linked through a single weak C—H⋯O hydrogen bond, forming ribbons which extend along (100), giving alternating zigzag molecular layers which stack down the b-axis direction.

Related literature

For applications of similar structures see: Chandrasekhar et al. (2007 ▶); Varma & Saini (1997 ▶); Donnelly & Farrell (1990 ▶); Hemanth Kumar et al. (2004 ▶). For the synthesis of the 2-aminochalcone, see: Gao et al. (1996 ▶). For related structures, see: Bouraiou et al. (2008 ▶, 2011 ▶); Belfaitah et al. (2006 ▶); Benzerka et al. (2011 ▶). graphic file with name e-68-o1701-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₅ClN₂O
M _r = 322.78
Orthorhombic,
a = 13.8912 (8) Å
b = 12.4572 (4) Å
c = 17.8617 (11) Å
V = 3090.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
6664 measured reflections
3537 independent reflections
1696 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.169
S = 1.00
3537 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020831/zs2200sup1.cif

e-68-o1701-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020831/zs2200Isup2.hkl

e-68-o1701-Isup2.hkl^{(170KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020831/zs2200Isup3.cml

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
C17—H17⋯O1ⁱ	0.93	2.49	3.243 (5)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to all personal of PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are due to MESRS and ANDRU (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique et l’Agence Nationale pour le Développement de la Recherche Universitaire) (Algeria) via the PNR programm for financial support.

supplementary crystallographic information

Comment

2-Substituted dihydroquinolinones have important medicinal properties as new chemical entities and also serve as building blocks for creating further diversity in SAR studies in various therapeutic areas (Chandrasekhar et al., 2007). Convenient synthesis of 2-aminochalcone and its amide derivatives and the ready cyclization of these compounds to 2-aryl-2,3-dihydroquinolin-4(1H)-ones have been widely explored (Varma & Saini, 1997; Donnelly & Farrell, 1990). Silica gel supported InCl₃ (20 mol %) is a new solid-support catalyst that can be used under solvent-free conditions for the facile and efficient isomerization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones (Hemanth Kumar et al., 2004). As a part of a program directed toward the synthesis of new suitably functionalized heterocyclic compounds of potential biological activity (Bouraiou et al., 2008, 2011; Benzerka et al., 2011), we report herein the synthesis and structure determination of the title compound, C₁₉H₁₅ClN₂ O.

In the title compound (Fig. 1), the quinoline ring forms a dihedral angle of 43.24 (1)° with the phenyl ring of the 2,3-dihydroquinolin-4(1H)-one moiety. The geometric parameters are in agreement with those of other structures possessing a quinolyl substituent, previously reported in the literature (Belfaitah et al., 2006; Benzerka et al., 2011). The crystal structure can be described as alterning zigzag ribbons which stack down the b axis of the unit cell (Fig. 2), these ribbons comprising molecules linked through a single weak intermolecular C17—H···O1 hydrogen bond (Table 1), and extending down a (Fig. 3). The hetero N2—H2 group has no acceptor in the crystal structure.

Experimental

2-Aminoacetophenone (1mmol) was first condensed with 2-chloro-3-formyl-6-methylquinoline (2 mmol) to give the corresponding 2-aminochalcone in 74% yield, according to the procedure described by Gao et al. (1996). In the next step, a mixture of 2-aminochalcone (100 mg) and 1 g of silica gel impregnated with indium(III) chloride (20 mol%, 13.6 mg) was irradiated in a domestic microwave oven at 360 W for 5 minutes. Under these conditions, the title compound was successfully synthesized in good yield (69%). Single crystals suitable for the X-ray diffraction analysis were obtained by dissolving the compound in a diisopropyl ether/CHCl₃ solvent mixture and allowing the solution to slowly evaporate at room temperature.