3-(2-Hydroxy­ethyl)-2-(p-tolyl­amino)­quinazolin-4(3H)-one

Gui-Fu Zhang; Zuan Ma; Xu-Hong Yang

doi:10.1107/S1600536808040440

. 2008 Dec 6;65(Pt 1):o34–o35. doi: 10.1107/S1600536808040440

3-(2-Hydroxyethyl)-2-(p-tolylamino)quinazolin-4(3H)-one

Gui-Fu Zhang ^a, Zuan Ma ^b, Xu-Hong Yang ^a,^*

PMCID: PMC2967952 PMID: 21581677

Abstract

In the title compound, C₁₇H₁₇N₃O₂, the quinazolinone ring system is essentially planar. The benzene ring is twisted with respect to it by a dihedral angle of 32.7 (5)°. The molecular conformation is stabilized by an N—H⋯O hydrogen bond, and the crystal structure is stabilized by intermolecular O—H⋯N interactions.

Related literature

For the biological properties of quinazolinone derivatives, see: Pandeya et al. (1999 ▶); Shiba et al. (1997 ▶), Malamas & Millen (1991 ▶); Mannschreck et al. (1984 ▶); Kung et al. (1999 ▶); Bartroli et al. (1998 ▶); Palmer et al. (1997 ▶); Tsou et al. (2001 ▶); Matsuno et al. (2002 ▶). For the synthesis, see: Yang et al. (2008 ▶). For related structures, see: Hu et al. (2006 ▶); Qu et al. (2008 ▶); Zeng et al. (2008 ▶); Sun et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₇N₃O₂
M _r = 295.34
Monoclinic,
a = 7.8589 (2) Å
b = 19.1706 (5) Å
c = 10.6696 (3) Å
β = 111.082 (3)°
V = 1499.89 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.981, T _max = 0.993
15404 measured reflections
2938 independent reflections
2074 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.138
S = 1.07
2938 reflections
206 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040440/bt2827sup1.cif

e-65-00o34-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040440/bt2827Isup2.hkl

e-65-00o34-Isup2.hkl^{(144.2KB, 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
O1—H1D⋯N3ⁱ	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1⋯O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Xianning College for financial support of this work and for providing laboratory and analytical facilities. The authors also acknowledge Dr Xiang-Gao Meng, Central China Normal University Whuhan, for the data collection.

supplementary crystallographic information

Comment

The synthesis of derivatives of quinazolinone has been the focus of great interest. This is due, in part, to the broad spectrum of biological properties of these compounds. Some of these activities include antimicrobial (Pandeya et al., 1999; Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al., 2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. The compound (Fig. 1), may be used as a new precursor for obtaining bioactive molecules. The bond lengths and angles are unexceptional. The quinazolinone ring system is almost planar, with a maximum deviation of 0.037Å for N2; the phenyl ring is twisted with respect to it, with a dihedral angle of 32.7 (5)°. Intramolecular N—H···O and intermolecular O—H···N hydrogen bonds (Fig. 2 and Table 2) stabilize the molecular conformation and the crystal structure.

Experimental

To a solution of 1-(4-methyl-phenyl)- 3-(2-ethoxycarbonylphenyl) carbodiimide (3 mmol) in THF (15 ml) was added 2-aminoethanol (3 mmol). After the reaction mixture was allowed to stand for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 4 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound. The product was recrystallized from methanol-dichloromethane (1:1 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction.