2-(4-Chloro­anilino)-3-(2-hydroxy­ethyl)quinazolin-4(3H)-one

Hong-Ling Wang; Xu-Hong Yang; Ming-Hu Wu

doi:10.1107/S1600536808036623

. 2008 Nov 13;64(Pt 12):o2325. doi: 10.1107/S1600536808036623

2-(4-Chloroanilino)-3-(2-hydroxyethyl)quinazolin-4(3H)-one

Hong-Ling Wang ^a, Xu-Hong Yang ^a, Ming-Hu Wu ^a,^*

PMCID: PMC2959957 PMID: 21581300

Abstract

In the title molecule, C₁₆H₁₄ClN₃O₂, the dihedral angle between the chlorophenyl and pyrimidinone rings is 14.8 (1)°, while the dihedral angle between the fused benzene ring and the pyrimidinone ring is 3.8 (1)°. In the crystal structure, intramolecular N—H⋯O hydrogen bonds, together with intermolecular O—H⋯O hydrogen-bonding interactions, are present.

Related literature

For the biological activities and applications of 4(3H)-quinazolinone, see: Armarego (1963 ▶); Fisnerova et al. (1986 ▶); Gravier et al. (1992 ▶). For details of our ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂
M _r = 315.75
Monoclinic,
a = 9.0707 (18) Å
b = 11.345 (2) Å
c = 14.143 (3) Å
β = 96.98 (3)°
V = 1444.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 273 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.947, T _max = 0.973
8113 measured reflections
2824 independent reflections
2300 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.05
2824 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶; data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036623/ez2147sup1.cif

e-64-o2325-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036623/ez2147Isup2.hkl

e-64-o2325-Isup2.hkl^{(138.7KB, 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
N1—H1A⋯O2	0.839 (18)	1.993 (19)	2.8017 (19)	161.8 (17)
O2—H2A⋯O1ⁱ	0.86 (2)	1.86 (2)	2.7180 (18)	174 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefully acknowledge financial support of this work as a project of the Natural Science Foundation of Hubei Province under grant No. 2006ABA334.

supplementary crystallographic information

Comment

One of the most frequently encountered heterocyclic molecules in medicinal chemistry is 4(3H)-quinazolinone, which has wide application as a result of antibacterial, antifungal, anticonvulsant, and anti-inflammatory activities (Armarego, 1963; Gravier et al., 1992; Fisnerova et al., 1986). In our ongoing heterocyclic synthesis and drug discovery project (Yang et al., 2008) we have focused on the synthesis of quinazolinones and pyrazolo pyrimidinones. Herein, the title compound was synthesized and determined by single-crystal X-ray diffraction.

In the molecule (Fig. 1), the dihedral angle between the chlorophenyl and pyrimidinone rings is 14.8 (1)°, and the dihedral angle between the fused benzene and pyrimidinone rings is 3.8 (1)°.

In the crystal structure, molecules are linked by intramolecular N1–H1A···O2 hydrogen-bonds together with O2–H2A···O1ⁱ intermolecular hydrogen-bonding interactions (symmetry code: i, -1/2 - x,1/2 + y,3/2 - z) (Fig. 2).

Experimental

To a solution of 2-ethoxycarbonyliminophosphorane (1.27 g, 3 mmol) in 10 ml absolute anhydrous CH₂Cl₂, 4-chlorophenylisocyanate (0.46 g, 3 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter a solution of 2-hydroxyethylamine (0.18 g, 3 mmol) in 5 ml absolute anhydrous CH₂Cl₂was added. The reaction mixture was then stirred overnight, the solution cooled and the reaction product recrystallized from CH₃OH to give colorless crystals of the title compound suitable for X-ray analysis in 58% yield.