Hydrochloric Acid → HCID 20523547, compound

Participants

Reaction Steps

A mixture of 4.82 g (0.014 mole) of the 2-[(2-phenyl-3-indolyl)carbonyl]benzoic acid from part A above, 3.60 g (0.02 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine, and five ml of acetic anhydride was slowly heated until a purple color formed and maintained at this temperature for approximately two hours. After cooling to room temperature, sufficient 3 N hydrochloric acid was added to the mixture to effect solution and stirring was continued for approximately 1.5 hours. The resulting solution was filtered and the pH adjusted to five by the addition of sodium acetate. The precipitate which separated from the solution was collected by filtration and dried to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(2-phenyl-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =R6 =Y1 =H; R=CH3 ; R4 =N(CH3)2 ; R5 =C6H5). After recrystallization from toluene and hexane, the off white-colored solid melted at 153°-155° C. Significant infrared maxima were observed at 3380 cm-1 (NH; m) and 1750 cm-1 (C=O; s). The nuclear magnetic resonance spectrum was consistent with the structure. A toluene solution of this product spotted on silica gel developed an intense grape-red-colored image.

Provenance & Evidence