Formic Acid → HCID 15918615, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.0 g of Azure B (Aldrich) 7-(dimethylamino)-3-(methylamino)phenothiazin-5-ium chloride, 75.0 ml of 90 percent formic acid, 5.0 g of zinc dust and 5.0 ml of pyridine was maintained at approximately 90° C. for approximately three hours. The reaction mixture was cooled to room temperature and filtered, saving the filtrate. The filter cake was washed twice, each time with 50.0 ml of acetone, and the washes combined with the filtrate. The combined filtrate and washes was poured into ice water with stirring. The resulting solution was extracted with toluene. The toluene solution was separated, treated with decolorizing carbon, filtered and the resulting solution was evaporated under reduced pressure to obtain a gummy residue. The gummy residue was titurated with a 1:1 (V:V) mixture of isopropyl alcohol and hexane. The solid which formed was collected by filtration and dried to obtain 0.14 g of 7-(dimethylamino)-3-(N-formyl-N-methylamino)-10-formylphenothiazine (Formula II: R=R1 =R5 =H; R2 =R3 =R4 =CH3), an off-white-colored powder which melted at 139° to 143° C. A significant infrared maximum appeared at 1685 cm-1 (C=O; s). A paper treated with an ink formulation of the product produced a black-colored image when traced with an applied voltage stylus.

Provenance & Evidence