Ammonia → 1H-Naphth[2,3-f]isoindole-1,3,5,10(2H)-tetrone, 4,11-diamino-2-[3-(2-methoxyethoxy)propyl]-

Participants

Reaction Conditions

Reaction Steps

477.2 g of 3-(2-methoxyethoxy)propylamine are charged to a 750 ml sulfonating flask equipped with paddle stirrer and heated to 40° C. With stirring, 141.2 g of 1,4-diaminoanthraquinone-2,3-dicarboximide are added over 11/4 hours. The ensuing reaction is slightly exothermic, with evolution of NH3. The reaction mixture is heated to 40° C. and further stirred at this temperature for 2 hours. The suspension is then cooled to 20° C. and stirred for a further hour at this temperature and filtered with suction. The filter cake is washed with 300 ml of methanol and then with 300 ml of water, affording 246.3 g of N-[3-(2-methoxyethoxy)propyl]-1,4-diaminoanthraquinone-2,3-dicarboximide with a solids content of 74.7%, corresponding to 180.1 g of this compound (100%). After optional replenishment with fresh 3-(2-methoxyethoxy)propylamine, the mother liquor can be re-used repeatedly.

Provenance & Evidence