Potassium Iodide → HCID 22624024, compound

Participants

Reaction Steps

2-Chloro-N,N-dimethylethylamine hydrochloride (0.5 g, 3.3 mmol), potassium iodide (0.4 g, 2.4 mmol), and potassium carbonate (1.4 g, 10.1 mmol) were added to a suspension of 2-benzyloxy-5-hydroxy-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.5 mmol) in acetone (100 mL). The mixture was refluxed for 8 hours and concentrated in vacuo. The residue was dissolved in water and extracted with 30% methanol in chloroform. The organic layer was dried (Na2SO4), filtered, and concentrated to give 0.3 g of 2-benzyloxy-5-(2-dimethylamino-ethoxy)-benzo[de]isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-5-(2-dimethylamino-ethoxy)-benzo[de]isoquinoline-1,3-dione (0.2 g) in the presence of 10% Pd/C (0.2 g) in DMA (20 mL) afforded 0.04 g of the title compound, mp 225-229° C.;

Provenance & Evidence