Potassium Hydroxide → 6-Phenyl-2-(quinolin-6-ylmethyl)pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a 25 mL round-bottomed flask containing 6-(bromomethyl)quinoline (0.35 g, 1.6 mmol) was added benzene (10 mL), 6-phenyl-3(2H)-pyridazinone (0.15 g, 0.87 mmol, Aldrich), tetrabutylammonium bromide (0.056 g, 0.17 mmol) and potassium hydroxide (0.15 g, 2.6 mmol). The mixture was stirred at 25° C., then poured into aq. NaHCO3 (100 mL) and extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.050 g, 18% yield). MS (ESI pos. ion) m/z (MH+): 314. Calc'd exact mass for C20H15N3O: 313. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (dd, J=4.2, 1.7 Hz, 1 H), 8.38 (dd, J=8.4, 0.8 Hz, 1 H), 8.11 (d, J=9.6 Hz, 1 H), 8.01 (d, J=8.6 Hz, 1 H), 7.88-7.93 (m, 3 H), 7.78 (dd, J=8.8, 2.0 Hz, 1 H), 7.43-7.54 (m, 4H), 7.13 (d, J=9.8 Hz, 1 H), 5.54 (s, 2 H).

Provenance & Evidence