Potassium Carbonate → 3-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzonitrile

Participants

Reaction Steps

Prepared by coupling 3-cyanophenylboronic acid with an equivalent amount of 6-bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one using a catalytic amount of tetrakis(triphenylphosphine)palladium(0) as a catalyst with overnight refluxing in toluene containing an equivalent amount of potassium carbonate dissolved in water in the usual manner followed by recrystallization from ethanol gave a gray solid: mp. 190-192° C.; 1H-NMR (DMSO-d6) δ 10.29 (s, 1H), 8.17 (s, 1H), 8.00 (d, 1H, J=7.9 Hz), 7.77 (d, 1H, J=6.4 Hz), 7.65 (m, 2H), 7.55 (d, 1H, J=8.2 Hz), 6.97 (d, 1H, J=8.3 Hz), 2.40 (s, 2H), 1.30 (s, 6H); MS (APCI(−)) m/z 275 [M−H]− Anal. Calc. For C18H16N2O 0.25H2O: C, 75.77, H, 6.01, N, 9.82. Found: C, 75.45, H, 5.65, N, 920.

Provenance & Evidence