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

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.

In the title compound, C 17 H 17 N 3 O 2 , 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-HÁ Á ÁO hydrogen bond, and the crystal structure is stabilized by intermolecular O-HÁ Á ÁN interactions.

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 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 2aminoethanol (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.

Refinement
All H atoms were located in difference maps. Those bonded to C were treated as riding atoms with C-H = 0.93 Å, U iso =1.2U eq (C) for Csp 2 , C-H = 0.97 Å, U iso = 1.2U eq (C) for CH 2 . The coordinates of the H atoms bonded to N and O were refined with a distance restraint of O-H = 0.88 (2)Å and U iso = 1.2U eq (O, N). Fig. 1. View of the molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. 3-(2-Hydroxyethyl)-2-(p-tolylamino)quinazolin-4(3H)-one

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.