Hydrazine hydrate (1:1) → NSC349455

Participants

Reaction Conditions

Reaction Steps

With stirring, a mixture of 1200.0 ml of 80 percent aqueous ethyl alcohol, 25.0 g of 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide and 35.4 g of 85 percent hydrazine hydrate was maintained at reflux temperature, approximately 90° C., for approximately three hours. After setting overnight at ambient temperature, the resulting slurry was chilled to approximately 5° C. by means of an external ice bath. The solid was collected by filtration, washed four times each with 50.0 ml of cold water and air-dried to obtain 20.8 g of 4,4-bis(4-dimethylaminophenyl)-7-dimethylaminophthalazin-1(2H)-one (Formula III: R=N(CH3)2 ; R1 =R3 =R9 =H; R4 =R5 =R10 =R11 =CH3), a white-colored solid which melted at 265°-270° C. Significant infrared maxima appeared at 1660 cm-1 (C=O;s) and 3400 cm-1 (N-H;m). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper treated with an ink formulation of the product produced a blue-green-colored image when traced with an applied voltage stylus.

Provenance & Evidence