p-Toluenesulfonic acid → 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline

Participants

Reaction Steps

To a solution of N-benzhydrylidene-N′-isoquinolin-5-yl-hydrazine 4A (1.4 mmol) and acetophenone (2.1 mmol) in EtOH (7 mL), pTSA (5.6 mmol) was added and the mixture was submitted to microwaves at 120° C. for 1 h. The solvent was removed, the residue was dissolved in DCM and washed with aq saturated NaHCO3. The organic layer was dried (Na2SO4) and concentrated. The crude material was then purified by chromatography on silica gel (eluant: hexane/AcOEt 4:6) affording the title compound (58% yield). ESI (+) MS: m/z 245 (MH+). 1H NMR (500 MHz): 7.16 (d, J=2.20, 1H), 7.37 (t, J=7.45, 1H), 7.53 (t, J=7.81, 2H), 7.63 (d, J=8.79, 1H), 7.83 (d, J=8.79, 1H), 8.00 (d, J=7.32, 2H), 8.44 (d, J=5.62, 1H), 8.56 (d, J=5.62, 1H), 9.22 (bs, 1H), 12.40 (bs, 1H).

Provenance & Evidence