Water → HCID 59843000, compound

Participants

Reaction Conditions

Reaction Steps

(reference: Synthesis 1981, 631). To a solution containing 6-(2-bromoethyl)quinoline (0.13 g, 0.56 mmol) in benzene (6.0 mL) was added 6-phenyl-3(2H)-pyridazinone (0.096 g, 0.56 mmol, Aldrich), tetrabutylammonium bromide (0.036 g, 0.11 mmol) and potassium hydroxide (0.094 g, 1.7 mmol). The mixture was stirred at 25° C. for 20 h, then poured into water (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 to 3.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.12 g, 63% yield). MS (ESI pos. ion) m/z (MH+): 328. Calc'd exact mass for C21H17N3O: 327. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83 (dd, J=4.2, 1.7 Hz, 1 H), 8.25 (dd, J=8.3, 0.9 Hz, 1 H), 7.98 (d, J=9.8 Hz, 1 H), 7.94 (d, J=8.6 Hz, 1 H), 7.78 (d, J=1.4 Hz, 1 H), 7.65-7.71 (m, 3H), 7.47 (dd, J=8.3, 4.2 Hz, 1 H), 7.36-7.42 (m, 3 H), 7.02 (d, J=9.8 Hz, 1 H), 4.51 (t, J=7.2 Hz, 2 H), 3.31 (t, J=7.0 Hz, 2 H).

Provenance & Evidence