Reaktion #93823

Reaktionsgleichung

palmityl chloride

1-palmitylamino-8-amino-4,5-dihydroxyanthraquinone

1-amino-8-nitro-4,5-dihydroxyanthraquinone

hydrazine hydrate

Ammonia

phenol

boric acid

→

1,4-diamino-5-hydroxy-8-palmitylaminoanthraquinone

Lösungsmittel

water

toluene

nitrobenzene

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeformed
2. 2
   Sonstigethereby being removed from the system
3. 3
   workup.DISTILLATIONThe toluene is then distilled off
4. 4
   workup.ADDITIONare added
5. 5
   TemperaturThe reaction mixture is cooled to 90° C.
6. 6
   TemperaturAfter cooling to room temperature
7. 7
   Sonstigethe dye precipitated
8. 8
   Filtrationis filtered off with suction
9. 9
   Waschenthe material on the filter is washed with methanol and water
10. 10
    Sonstigedried

Vorschrift

120 parts of phenol, 6.1 parts (0.1 mole) of boric acid and 70 parts of toluene are refluxed, while stirring, the water of reaction formed thereby being removed from the system. The toluene is then distilled off, the mixture is cooled to 110° C. and 25.4 parts (0.05 mole) of 1-palmitylamino-8-amino-4,5-dihydroxyanthraquinone (prepared by reacting 1-amino-8-nitro-4,5-dihydroxyanthraquinone with palmityl chloride in nitrobenzene and then reducing the product with hydrazine hydrate) are added. Ammonia is then passed in at this temperature until no further starting material can be detected in the thin-layer chromatogram (duration: 3 hours). The reaction mixture is cooled to 90° C. and 240 parts of methanol are added. After cooling to room temperature, the dye precipitated is filtered off with suction and the material on the filter is washed with methanol and water and dried. 20 parts of 1,4-diamino-5-hydroxy-8-palmitylaminoanthraquinone of melting point 174° C. are obtained.

Quelle