Water → 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one

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Reaction Steps

To a suspension of 1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate (1.70 g, 5.76 mmol), benzophenone hydrazone (1.36 g, 6.91 mmol), Cs2CO3 (2.81 g, 8.64 mmol) and DPPF (0.048 g, 0.086 mmol) in degassed PhMe (40 mL) was added Pd(OAc)2 (0.013 g, 0.058 mmol) and the resulting mixture was stirred at RT for 30 min and then heated at 90° C. After 16 h, the mixture was cooled to RT, H2O (50 mL) was added and the mixture was extracted with EtOAc (3×50 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one (980 mg, 50% yield). 1H NMR (400 MHz, acetone-d6): δ 8.69 (brs, 1H), 7.79 (d, J=9.2 Hz, 1H), 7.63-7.54 (m, 5H), 7.37-7.31 (m, 5H), 7.11-7.08 (m, 2H), 6.67 (brS, 1H), 3.47 (dt, J=7.2, and 3.2 Hz, 2H), 2.90 (t, J=6.6 Hz, 2H); MS (ESI) m/z: 342.0 (M+H+).

Provenance & Evidence