Dimethylformamide → 3H-Naphtho[1,2,3-de]quinoline-1-carbonitrile, 2,7-dihydro-6-[[4-(2-hydroxyethyl)phenyl]amino]-3-methyl-2,7-dioxo-

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Reaction Conditions

Reaction Steps

A sample of 6-bromo-1-cyano-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione (36.5 g of 96% assay material--35.0 g pure material, 0.10 m) prepared is in Example 2, p aminophenylethanol (55.0 g), potassium carbonate (10.0 g), cupric acetate (12.0 g) and N,N-dimethylformamide (100 ml) were mixed and heated at about 70° C. for 1 hr. The temperature was then increased to about 80° C. and held for 1 hr, increased to about 90° C. and held for 1 hr, increased to about 100° C. and held for 1 hr and finally increased to 110° C. and held for 2 hrs. Additional N,N-dimethylformamide (140 ml) and isopropanol (280 ml) were added at about 80° C. and the reaction mixture allowed to cool to room temperature. The product was collected by filtration, washed with isopropanol, water and again with isopropanol. After drying the product weighed 34.97 g (85.5% weight yield) and was determined to have an assay of 95.2% by high pressure liquid chromatography to give an assay yield of 0.952×0.855×100 or 8.13% of 1-cyano-6-[4-(2-hydroxyethyl)anilino]-3-methyl-3-H dibenz[f,ij]isoquinoline-2,7-dione. The product as produced was very pure and did not require further purification by recrystallization. The overall percent assay yield for the three steps, based on starting with 1-methylamino-4-bromo anthraquinone, Was 0.97×0.844×0.813×100 or 66.6%

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