Water → 2-Phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbaldehyde

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Reaction Steps

To a solution of 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline XIXA (2.75 mmol) in DCM (13 mL) and nitromethane (13 mL), cooled to 0° C., aluminum chloride (8.25 mmol) and dichloromethylmethylether (5.5 mmol) were added dropwise. The mixture was kept at 4° C. overnight and poured dropwise into stirred ice-cooled water. The solid product was filtered and the layers were separated. The aqueous layer was extracted with DCM and AcOEt. The combined organic layers, washed with water, dried (Na2SO4) and concentrated, were joined to the previously described solid affording the title compound in 51% yield. ESI (+) MS: m/z 273 (MH+). 1H NMR: 7.66-7.71 (m, 3H), 7.91-7.96 (m, 2H), 8.19 (d, J=8.79, 1H), 8.71 (d, J=8.55, 1H), 8.79 (d, J=6.35, 1H), 8.93 (d, J=6.35, 1H), 9.77 (s, 1H), 10.12 (s, 1H), 13.80 (bs, 1H).

Provenance & Evidence