Reaktion #55288

Reaktionsgleichung

sodium hydroxide

2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid

N,N,N',N'-tetramethyl-m-phenylenediamine

acetic anhydride

→

3-(2,4-bis(dimethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide

Lösungsmittel

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe resulting mixture was poured onto ice
2. 2
   SonstigeRecrystallization of the resulting product

Vorschrift

A mixture of 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (25 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (13.2 g.) and acetic anhydride (75 g.) was heated (to 95° C.) during one hour, then refluxed with dilute hydrochloric acid (32 g. concentrated hydrochloric acid plus 160 ml. water) during one and one-half hours. The resulting mixture was poured onto ice and the pH was adjusted to 6 with sodium hydroxide. Recrystallization of the resulting product afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)phthalide (I: X=(CH3)2N, Y2 =CH3, Y4 =(CH3CH2)2N, Z4 =Z5 =Z6 =Z7 =H) in a first crop from toluene (m.p. 204°-206° C.) and in a second crop from a mixture of toluene and hexane (m.p. 191°-195° C.).

Quelle