Ethanol → HCID 20268298, compound

Participants

Reaction Steps

With stirring, a mixture of 25.0 g of 3,3-bis(1-butyl-2-methylindol-3-yl)phthalide, 800.0 ml of ethyl alcohol, 200.0 ml of water and 29.4 g of 85 percent hydrazine hydrate was maintained at reflux temperature for approximately forty-eight hours. The resulting mixture was chilled in an external ice bath to a temperature in the range of 0°-5° C. The solid was collected by filtration, washed with chilled ethyl alcohol and dried in an air oven to obtain 23.65 g of 4,4-bis(1-butyl-2-methylindol-3-yl)-phthalazin-1(2H)-one (Formula V: R=R1 =R8 =R14 =H; R6 =R12 =C4H9 ; R7 =R13 =CH3), a pale orange-colored solid which melted at 205.5°-206.5° C. In the infrared spectrum maxima appeared at 3400 cm-1 (N-H;w) and 1670 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper treated with an ink formulation of the product produced a purple-colored image when traced with an applied voltage stylus.

Provenance & Evidence