Hydrochloric Acid → 3-(2,4-Bis(dimethylamino)phenyl)-3-(2-ethoxy-4-(diethylamino)phenyl)phthalide

Participants

Reaction Steps

A mixture of 2-(2-ethoxy-4-(diethylamino)benzoyl)benzoic acid (6.82 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (2.80 g.) and acetic anhydride (20 g.) was heated (70°-75° C.) during one hour, let stand overnight and poured into dilute hydrochloric acid. The resulting mixture was basified. Recrystallization of the resulting red precipitate from hexane followed by slurrying in alkaline water afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(2-ethoxy-4-(diethylamino)phenyl)phthalide (I: X = (CH3)2N, Y2 = CH3CH2O, Y4 = (CH3CH2)2N, Z4 = Z5 = Z 6 = Z7 = H) (m.p. 146°-150° C.).

Provenance & Evidence