Ethyl 2-methyl-4-phenylquinoline-3-carboxylate

In the molecule of the title compound, C19H17NO2, the quinoline ring system is planar [maximum deviation 0.021 (3) Å] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4)°. Intramolecular C—H⋯O interactions result in the formation of five- and six-membered rings having planar and envelope conformations, respectively. In the crystal structure, intermolecular C—H⋯O interactions link the molecules into centrosymmetric dimers forming R 2 2(12) ring motifs. π–π contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å] may further stabilize the structure. Two weak C—H⋯π interactions are also found.

In the molecule of the title compound, C 19 H 17 NO 2 , the quinoline ring system is planar [maximum deviation 0.021 (3) Å ] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4) . Intramolecular C-HÁ Á ÁO interactions result in the formation of five-and six-membered rings having planar and envelope conformations, respectively. In the crystal structure, intermolecular C-HÁ Á ÁO interactions link the molecules into centrosymmetric dimers forming R 2 2 (12) ring motifs.contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å ] may further stabilize the structure. Two weak C-HÁ Á Á interactions are also found.
dergo hierarchical self-assembly into a variety of nano and meso structures with enhanced electronic and photonic functions.
We report herein the synthesis and crystal structure of the title compound.

Experimental
For the preparation of the title compound, a mixture of ethyl acetoacetate (0.13 g, 1 mmol), (2aminophenyl)(phenyl)methanone (0.20 g, 1 mmol) and p-toluene sulfonic acid (0.1 g, 5.8 mmol) in water (5 ml) was stirred at reflux for 4 h. After completion of reaction (monitored by TLC) the reaction mixture was filtered and the precipitate washed with water (15 ml) and then recrystallized from EtOH/water (1:2) to afford the pure product (yield; 75%, 0.218 g).

Refinement
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C).