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

HRID 867964Notes

Reaction equation

HRID 867964 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][NH2:9].[NH2:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([NH2:27])=[C:13]2[C:28](=[O:32])N[C:30](=[O:31])[C:12]=12.N>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][N:9]1[C:28](=[O:32])[C:13]2[C:12](=[C:11]([NH2:10])[C:24]3[C:23](=[O:25])[C:22]4[C:17]([C:16](=[O:26])[C:15]=3[C:14]=2[NH2:27])=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:30]1=[O:31]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 671921,4-Diamino-2,3-anthraquinonedicarboximideHCID 1085741-Propanamine, 3-(2-methoxyethoxy)-

Product 1

HCID 1030861H-Naphth[2,3-f]isoindole-1,3,5,10(2H)-tetrone, 4,11-diamino-2-[3-(2-methoxyethoxy)propyl]-Yield 126.6%

Conditions

Temperature
40 °C

Procedure

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.

Workup

  1. customequipped with paddle stirrer
  2. customThe ensuing reaction
  3. temperatureThe reaction mixture is heated to 40° C.
  4. stirringfurther stirred at this temperature for 2 hours
  5. temperatureThe suspension is then cooled to 20° C.
  6. stirringstirred for a further hour at this temperature
  7. filtrationfiltered with suction
  8. washThe filter cake is washed with 300 ml of methanol

Sources & evidence

ORD record
ord-0f90947a4d144398992acc3ce4666c30
Source dataset
uspto-grants-1988_10
Patent number
US04777266

Reaction notes

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