Dimethylformamide → 1-Amino-4-hydroxyanthraquinone

HRID 1413421

Reaktionsgleichung

Reaktionsgleichung von HRID 1413421
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.CN(C)C=[O:23].[N-]=[N+]=[N-].[Na+]>O>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[C:7]([OH:23])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 67041-NitroanthraquinoneHCID 33557Sodium Azide

Produkt 1

HCID 83231-Amino-4-hydroxyanthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

127 parts of 1-nitroanthraquinone are suspended at room temperature in 1000 parts of dimethyl formamide. To this suspension are then added 35 parts of sodium azide. The reaction mixture is then stirred for 8 hours at room temperature and, after addition of 1000 parts of a mixture of ice and water, filtered. The filter cake is washed with water and the moist product (28% paste) is added in the course of 2 hours to 1000 parts of conc. sulfuric acid, taking care that the temperature does not rise above 85° C. The suspension is then heated to 95° C., stirred for 3 hours at 95°-100° C. and, after the dropwise addition of 400 parts of ice-water, filtered hot. The filtrate is then poured into 4000 parts of ice-water and filtered. The filter cake is washed neutral with water, affording 100 parts of 1-amino-4-hydroxyanthraquinone.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filter cake is washed with water
  3. additionthe moist product (28% paste) is added in the course of 2 hours to 1000 parts of conc. sulfuric acid
  4. customdoes not rise above 85° C
  5. temperatureThe suspension is then heated to 95° C.
  6. stirringstirred for 3 hours at 95°-100° C.
  7. additionafter the dropwise addition of 400 parts of ice-water
  8. filtrationfiltered hot
  9. additionThe filtrate is then poured into 4000 parts of ice-water
  10. filtrationfiltered
  11. washThe filter cake is washed neutral with water

Quellen und Nachweise

ORD-Eintrag
ord-d87c57f3e5364143ab8daa60d05569ed
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04250102

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