Ethanol, 1-bromo- → HCID 178518385, compound

Participants

Reaction Steps

2.34 g (18.75 mmol) of bromoethanol was added dropwise to a solution of 1.13 g (3.75 mmol) of 6-{[(E)-4-pyridinylmethylidene]amino}-1H-benzo[de]isoquinolin-1,3(2H)-dione in 60 mL of acetonitrile or acetone and the solution was then heated at reflux for 1 hour. After concentration to about ⅓ of the amount of solvent and cooling to room temperature, the resulting precipitate was suction-filtered off, washed with ethyl acetate and dried under vacuum. Yield: 0.59 g (37% of the theoretical), dark-yellow powder. 1H-NMR (d6-DMSO/300 MHz): δ=3.58 (t, J=13.5 Hz, 2H, ethyl); 4.01 (t, J=13.5 Hz, 2H, ethyl); 6.45 (s, 1H); 7.54-7.58 (m, 2H, aromatic); 7.19 (d, J=5.8 Hz, 2H, pyridyl); 8.40 (m, 1H, aromatic); 8.63 (d, J=5.8 Hz, 2H, pyridyl); 8.72-8.75 (m, 2H, aromatic); 11.39 (s, 1H, N—H).

Provenance & Evidence