Methanol → 2-Benzyloxy-6-methoxy-benzo[de]-isoquinoline-1,3-dione

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Reaction Steps

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (3.2 g, 8.4 mmol, from Example M) was added to a solution of sodium hydride (0.5 g, 12.5 mmol) in methanol (100 mL). The mixture was refluxed for 8 hours and concentrated in vacuo. The solid residue was dissolved in water and acidified with concentrated HCl to pH 4. The resulting precipitate was filtered, washed with water, and dried to give 0.8 g of 2-benzyloxy-6-methoxy-benzo[de]-isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-6-methoxy-benzo[de]isoquinoline-1,3-dione (0.6 g) in the presence of Pd/C (10%) in DMA (20 mL) afforded 0.2 g of the title compound, mp 267-269° C.;

Provenance & Evidence