Diphenylmethylidenehydrazine → N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-bromoisoquinoline (32 mmol), benzophenone hydrazone (32 mmol), BINAP (0.32 mmol) and palladium acetate (0.32 mmol) in dry and degassed toluene (15 mL), sodium tert-butoxide (44.9 mmol) was added together with 16 mL of dry, degassed toluene. The mixture was heated at 80° C. for 4 h, cooled to rt and filtered through a celite pad, rinsing with diethyl ether. The crude product was purified by semi -automatic liquid chromatography on silica gel (eluant: hexane/AcOEt 7:3) affording the title compound (65% yield). ESI (+) MS: m/z 324 (MH+). 1H NMR: 7.36 (d, J=6.10, 1H), 7.38-7.45 (m, 2H), 7.48-7.53 (m, 2H), 7.58 (m, 8H), 7.88 (d, J=6.34, 1H), 8.39 (d, J=5.97, 1H), 8.76 (s, 1H), 9.24 (s, 1H).

Provenance & Evidence