1-Nitroanthraquinone → Anthrimide

HRID 850902

Reaktionsgleichung

Reaktionsgleichung von HRID 850902
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]

Komponenten

5

Edukt 3

HCID 67041-NitroanthraquinoneHCID 67101-AminoanthraquinoneHCID 7047Quinoline

Produkt 1

HCID 6700Anthrimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-97d91443cf2c4235a940a4d347b10d7d
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382034

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