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1-Nitroanthraquinone → Anthrimide

HRID 850902
Notes
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Reaction equation

HRID 850902 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[NH2:11][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1.[N+]([C:31]1[C:44]2[C:43](=[O:45])[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36](=[O:46])[C:35]=2[CH:34]=[CH:33][CH:32]=1)([O-])=O>C(O)C>[CH:20]1[CH:19]=[C:18]2[C:17]([C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([NH:11][C:34]4[C:35]5[C:36]([C:37]6[C:42]([C:43](=[O:45])[C:44]=5[CH:31]=[CH:32][CH:33]=4)=[CH:41][CH:40]=[CH:39][CH:38]=6)=[O:46])[C:25]=3[C:24](=[O:26])[C:23]2=[CH:22][CH:21]=1)=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67041-NitroanthraquinoneHCID 67101-AminoanthraquinoneHCID 7047Quinoline

Product 1

HCID 6700Anthrimide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

250 ml of quinoline, 100 g of 1-aminoanthraquinone and 25 g of CaO are warmed to 200° to 210° C. in a 1 l sulphonation beaker with an anchor stirrer and shortpath distillation bridge. 120 g of 1-nitroanthraquinone are added in portions in the course of 2 hours, and the mixture is then stirred for another 5 hours at 200° to 210° C. The mixture is allowed to cool to 120° C., and is diluted slowly and under reflux with 500 ml of ethanol. The mixture is then filtered off under suction, and the residue is washed with ethanol and dried. The dry caked filter residue is heated under reflux in 1 l of water with 100 g of ammonium chloride, and is acidified slowly through the reflux condenser with concentrated hydrochloric acid. After filtering off the mixture under suction, washing the residue until the runnings are neutral, and drying, 190.4 g of 80.4% strength 1,1'-dianthraquinonylamine are obtained.

Workup

  1. additionis diluted slowly
  2. filtrationThe mixture is then filtered off under suction
  3. washthe residue is washed with ethanol
  4. customdried
  5. temperatureThe dry caked filter residue is heated
  6. temperatureunder reflux in 1 l of water with 100 g of ammonium chloride
  7. filtrationAfter filtering off the mixture under suction
  8. washwashing the residue until the runnings
  9. customdrying

Sources & evidence

ORD record
ord-97d91443cf2c4235a940a4d347b10d7d
Source dataset
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04382034

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes