Graveoline

Solid

Solid

Graveoline is a member of quinolines.

To a stirred solution of 2-benzo[1, 3]dioxol-5-yl-1H-quinolin-4-one (6) (100 mg, 0.37 mmol) in N, N-Dimethyl formamide (5 mL) at room temperature under a dry N2 atmosphere, potassium carbonate (156 mg, 1.1 mmol) and methyl iodide (80 mg, 0.56 mmol) were added at room temperature. The reaction mixture was heated and stirred at 80 °C for 5 h. After completion (monitored by TLC), the mixture was then quenched with water and extracted with dichloromethane (315 mL). It was dried over anhydrous Na2SO4 and after evaporation of the solvent under reduced pressure, the crude product were purified by recrystallization from ethyl acetate to get Graveoline 100 mg (95percent) as an off-white solid. mp. 188.6–191.4 °C; IR (KBr, cm1):1621, 1599, 1490, 1446, 1251, 1032, 751; Mass for C17H13NO3[M1], found 280.3; 1H NMR (400 MHz, CDCl3) (d ppm): 3.60 (s, 3H), 5.99 (s, 1H), 6.14 (s, 2H), 7.02 (d, 1H, J7.2 Hz), 7.08 (d, 1H, J8.0 Hz), 7.17 (s, 1H), 7.42–7.46 (m, 1H), 7.79 (d, 2H, J3.6 Hz), 8.22 (d, 1H, J8.0 Hz).; 13 C NMR (100 MHz, CDCl3) (d ppm); 37.35, 101.72, 108.64, 109.00, 112.64, 116.04, 122.76, 123.68, 126.68, 126.81, 129.43, 132.37, 141.97, 147.94, 148.77, 154.44, 177.59. The obtained product 1H and 13 C values are matched with standard values.[16]

Molecular Weight:279.29
XLogP3:3.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:279.08954328
Monoisotopic Mass:279.08954328
Topological Polar Surface Area:38.8
Heavy Atom Count:21
Complexity:461
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes