7-Fluoro-6-nitro­quinazolin-4(3H)-one

Yundeng Wu; Ancheng Ji; Aihua Zhang; Yipeng Shen

doi:10.1107/S1600536809046984

. 2009 Nov 14;65(Pt 12):o3075. doi: 10.1107/S1600536809046984

7-Fluoro-6-nitroquinazolin-4(3H)-one

Yundeng Wu ^a,^b, Ancheng Ji ^b, Aihua Zhang ^b,^*, Yipeng Shen ^b

PMCID: PMC2972082 PMID: 21578805

Abstract

The quinazolinone unit of the title compound, C₈H₄FN₃O₃, is essentially planar, with a maximum deviation of 0.0538 (14) Å for the O atom. The nitro group is twisted by 12.0 (3)° from the mean plane of the quinazolinone ring system. The crystal structure is stabilized by intermolecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds.

Related literature

The title compound is used as an intermediate for the production of several multi-targeted Raf kinase inhibitors, such as 4(3H)-quinazolinone and its derivatives, see: Bridges et al. (1996 ▶); Kim et al. (2008 ▶). For the antitumor activities of quinolines, see: Labuda et al. (2009 ▶). For synthetic aspects, see: Rewcastle et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-65-o3075-scheme1.jpg

Experimental

Crystal data

C₈H₄FN₃O₃
M _r = 209.14
Triclinic,
a = 5.6360 (11) Å
b = 8.409 (2) Å
c = 8.674 (2) Å
α = 79.38 (3)°
β = 89.23 (3)°
γ = 83.83 (3)°
V = 401.70 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.956, T _max = 0.971
1623 measured reflections
1461 independent reflections
1131 reflections with I > 2σ(I)
R _int = 0.018
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.160
S = 1.00
1461 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046984/pv2231sup1.cif

e-65-o3075-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046984/pv2231Isup2.hkl

e-65-o3075-Isup2.hkl^{(72KB, 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⋯O1ⁱ	0.86	1.98	2.815 (2)	165
C1—H1B⋯O2ⁱⁱ	0.93	2.47	3.396 (3)	179
C7—H7A⋯N2ⁱⁱⁱ	0.93	2.50	3.422 (3)	171

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

Acknowledgments

This research work was supported financially by the Research Funds of Jiangsu Provincial Institute of Materia Medica (No. SX200801).

supplementary crystallographic information

Comment

4(3H)-Quinazolinone and its derivatives have been investigated extensively, owning to their important role in the synthesis of several multi-kinase inhibitors and to their potentially beneficial antitumor activities in many types of malignancies (Labuda et al., 2009).

As part of our studies on the synthesis of 4(3H)-quinazolinone and its derivatives, the title compound, (I), which is used as the key intermediate (Rewcastle et al., 1996), has been synthesized in our laboratory. We report herein the crystal structure of the title compound.

The molecule of the title compound is planar (Fig. 1). The quinazolinone moiety is essentially planar with maximum deviation for for any atoms being 0.0538 (14) for O1. The nitro group is twisted from the mean-plane of the quinazolinone ring by 12.0 (3)°. The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The crtstal structure of (I) is stabilized by classical and non-classical intermolecular hydrogen bonds of the types N—H···O, C—H···N and C—H···O; details have been provided in Table 1 and presented as a packing diagram in Fig. 2.

Experimental

The title compound, was prepared by following a reported procedure (Rewcastle et al., 1996). 7-Fluoroquinazolin-4(3H)-one (47.4 g, 0.29 mmol) was added to a mixture of concentrated H₂SO₄ (100 ml) and fuming HNO₃ (100 ml), and heated at 373 K for 1 h. The crude product, 7-fluoro-6-nitroquinazolin-4(3H)-one, was obtained by pouring the reacting mixture onto ice-water (1500 ml). The crystals of (I) suitable for X-ray diffraction studies were obtained by recrystallization from acetic acid.