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

Qian Zhang; Yuan-Hong Jiao; Bin Liu; Xue-Mei Chen; Min Ruan; Ling-Hua Xu

doi:10.1107/S1600536809006254

. 2009 Feb 28;65(Pt 3):o638. doi: 10.1107/S1600536809006254

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

Qian Zhang ^a, Yuan-Hong Jiao ^a,^*, Bin Liu ^a, Xue-Mei Chen ^a, Min Ruan ^a, Ling-Hua Xu ^a

PMCID: PMC2968625 PMID: 21582287

Abstract

The molecular and crystal structures of the title compound, C₁₆H₁₄FN₃O₂, are stabilized by intramolecular N—H⋯O and intermolecular O—H⋯O hydrogen bonds. The existence of non-classical intramolecular C—H⋯N hydrogen bonds provides a dihedral angle between the fluoro-substituted benzene and pyrimidinone rings of 7.9 (1)°.

Related literature

For the pharmacological activity of N3 and C7 disubstituted quinazolines, see: Usha et al. (2006 ▶). For the synthesis of quinazolinone and thienopyrimidinones, see: Yang et al. (2008 ▶). For synthesis, drug discovery and crystal structures, see: Yang & Wu (2008 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₄FN₃O₂
M _r = 299.30
Monoclinic,
a = 8.5737 (8) Å
b = 10.8268 (10) Å
c = 15.2490 (13) Å
β = 104.070(10)°
V = 1371.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8342 measured reflections
2976 independent reflections
2475 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.102
S = 1.06
2976 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006254/rk2120sup1.cif

e-65-0o638-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006254/rk2120Isup2.hkl

e-65-0o638-Isup2.hkl^{(146.1KB, 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
C5—H5⋯N3	0.93	2.28	2.8807 (16)	122
N1—H1⋯O2	0.881 (9)	1.982 (10)	2.8253 (14)	159.7 (13)
O2—H2A⋯O1ⁱ	0.837 (9)	1.909 (10)	2.7426 (13)	173.6 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge financial support by the Huangshi Institute of Technology (grant Nos. 08yjz23B & 07yjz18B), P. R. China.

supplementary crystallographic information

Comment

Quinazolone derivatives have evoked considerable attention in recent years as these are endowed with wide range of pharmaceutical activities. 3H–Quinazolin–4–one represents a useful nucleus for preparation of some new sedative/hypnotic and anticonvulsant agents. Of the various quinazolines reported, the N3 and C7 disubstituted quinazolines exhibit interesting pharmacological activities like analgesic, anti–inflammatory, antibacterial and anticonvulsant activities (Usha et al., 2006). In connection with our ongoing heterocyclic synthesis and drug discovery project (Yang & Wu, 2008), we have focused on the synthesis of quinazolinone and thienopyrimidinones (Wang et al., 2008; Yang et al., 2008). Herein, the title compound was synthesied and its molecular (Fig. 1) and crystal structures were determined. An intramolecular N1—H1···O2 and non–classical C5—H5···N3 hydrogen bonds provide the conformation of the molecule - dihedral angle between the fluoro–substituted benzene ring and pyrimidinone rings as 7.9 (1)°. In the crystal structure, intermolecular O2—H2a···O1ⁱ hydrogen bonds link of molecules into chains (see Tab. 1 and Fig. 2). Symmetry code: (i) -x+5/2, y-1/2, -z+1/2.

Experimental

To a solution of 2–ethoxycarbonyliminophosphorane (1.27 g, 3.0 mmol) in 10 ml anhydrous THF, 4–fluorophenyl isocyanate (0.41 g, 3.0 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter the above resulting solution was added dropwise to a solution of ethanolamine (0.18 g, 3 mmol) in 5 ml anhydrous THF. The reaction mixture was stirred overnight at room temperature, the solvent was removed under reduced pressure and the residue was recrystallized from C₂H₄Cl₂/CH₃OH (1:1/v:v) to give colourless crystals of the title compound. Yield 89%.