Hydrochloric Acid → 9,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

HRID 226251

Reaktionsgleichung

Reaktionsgleichung von HRID 226251
N[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](N)[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1.S([O-])(O)=[O:22].[Na+].Cl.[OH-:27].[Na+]>>[CH2:4]1[C:5](=[O:20])[C:6]2[C:15](=[C:14]([OH:16])[C:13]3[C:8]([C:7]=2[OH:19])=[C:9]([OH:22])[CH:10]=[CH:11][C:12]=3[OH:17])[C:2](=[O:27])[CH2:3]1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673511,5-Diamino-4,8-dihydroxyanthraquinoneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 664859,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

Versuchsvorschrift

To crude 1,5-diamino-4,8-dihydroxyanthraquinone (11 g, 0.041 mol) was added NaOH (2.5 M, 200 mL) and the suspension was refluxed gently for 3 hours before it was allowed to cool down to room temperature. Sodium hydrogen sulphite (31.74 g, 0.182 mol) was added portionwise and the reaction mixture was refluxed again for 3 hours. It was cooled down to room temperature and was acidified with concentrated hydrochloric acid until pH 3. The precipitate was isolated by filtration and washed successively with cold water and then hot water. After lyophilisation overnight, the title compound was afforded as a crude brown solid (8 g, 73%). FAB MS, m/z(M+H)+ 251.

Aufarbeitung

  1. temperaturethe suspension was refluxed gently for 3 hours before it
  2. temperaturethe reaction mixture was refluxed again for 3 hours
  3. temperatureIt was cooled down to room temperature
  4. customThe precipitate was isolated by filtration
  5. washwashed successively with cold water

Quellen und Nachweise

ORD-Eintrag
ord-bfbc5450904d47cd921314288f591e6c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557215B2

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