2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one methanol monosolvate

In the title compound, C20H15N3O2·CH3OH, the quinazolinone ring system is approximately planar, the dihedral angle between the pyrimidinone ring and the adjacent benzene ring being 1.73 (6)°. The pyrimidinone ring makes dihedral angles of 77.58 (6) and 29.62 (6)°, respectively, with the hydroxyphenyl and phenyl rings. In the crystal, the components are connected by O—H⋯O and C—H⋯O hydrogen bonds, forming a zigzag chain along the b axis.

In the title compound, C 20 H 15 N 3 O 2 ÁCH 3 OH, the quinazolinone ring system is approximately planar, the dihedral angle between the pyrimidinone ring and the adjacent benzene ring being 1.73 (6) . The pyrimidinone ring makes dihedral angles of 77.58 (6) and 29.62 (6) , respectively, with the hydroxyphenyl and phenyl rings. In the crystal, the components are connected by O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds, forming a zigzag chain along the b axis.
In the crystal structure, the pyrimidinone heterocycle and the adjacent benzene ring are not planar, but inclined at 1.73 (6)°.
Significant intermolecular O-H···O and C-H···O and intramolecular O-H···O contribute strongly to the stability of the molecular configuration (Table 1 and Fig. 2).

Experimental
The title compound was prepared according to the literature method of Yang et al. (2008). To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added isocyanatobenzene (3 mmol) under nitrogen at room temperature.
After reaction, the mixture was allowed to stand for 10 h at 273-278 K, the solvent was removed under reduced pressure and diethyl ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed to give 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added 2-aminophenol (3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound, (I). The product was recrystallized from methanol-dichloromethane (1:1 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction (yield 85%).

Refinement
All C-bound H atoms were located at their ideal positions with C-H = 0.93 Å (aromatic) and 0.96 Å (methyl), and refined as riding, with U iso (H) = 1.2U eq (C) for aromatic and 1.5U eq (C) for methyl H atoms. H atoms bonded to N and O atoms were found in a difference map and then refined with distance restraints of N-H = 0.85 (2) Å and O-H = 0.90 (2) Å. The  Fig. 1. View of the molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.