Toluene → HCID 20268301, compound

Participants

Reaction Conditions

Reaction Steps

With stirring a mixture of 10.0 g of 3-(1-butyl-2-methylindol-3-yl)-3-(1-tetradecyl-2-methylindol-3-yl)phthalide, 9.4 g of 85 percent hydrazine hydrate and 50.0 ml of 2-ethoxyethanol was maintained at approximately 100° C. for approximately two hours. After cooling the reaction mixture to approximately 50° C., there was added slowly 75.0 ml of 5 percent aqueous ammonium hydroxide and 75.0 ml of toluene and a small portion of saturated sodium chloride solution. The water layer was separated and extracted a second time with 75.0 ml of fresh toluene. The two toluene portions were combined, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried toluene layer was then concentrated under vacuum to obtain 11.5 g of 4-(1-butyl-2-methylindol-3-yl)-4-(1-tetradecyl-2-methylindol-3-yl)phthalazin-1(2H)-one (Formula V: R=R1 =R8 =R14 =H; R6 =C4H9 ; R7 =R13 =CH3 ; R12 =C14H29), a thick dark brown oil which upon standing turned into a wax-like solid. A significant infrared maximum appeared at 1668 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 magenta-colored image when traced with an applied voltage stylus.

Provenance & Evidence