Cesium carbonate → HCID 59458312, compound

Participants

Reaction Steps

To a suspension of quinolin-6-yl trifluoromethanesulfonate (40 g, 0.14 mol), benzophenone hydrazone (35.6 g, 0.18 mol), cesium carbonate (74 g, 0.23 mol) and 1,1′-bis(diphenylphosphino)ferrocene (2.5 g, 4.5 mmol) in degassed toluene (1 L) was added palladium acetate (0.013 g, 0.058 mmol). The resultant mixture was heated to 90° C. under a nitrogen atmosphere. After 16 h, the mixture was concentrated in vacuo and the residue was purified through silica gel column chromatography (20-30% EtOAc in pet ether) to provide 1-(diphenylmethylene)-2-(quinolin-6-yl)hydrazine (32 g, 68.6% yield). 1H-NMR (300 MHz, DMSO-d6): δ 9.22 (s, 1 H), 8.58 (t, J=1.8 Hz, 1 H), 8.13 (d, J=3.6 Hz, 1 H), 7.80 (d, J=3.6 Hz, 1 H), 7.61 (d, J=3.9 Hz, 1 H), 7.59-7.51 (m, 4 H), 7.50 (d, J=3.6 Hz, 2 H), 7.33-7.39 (m, 6H); MS (ESI) m/z: 324 (M+H+).

Provenance & Evidence