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ChemicalBook CAS DataBase List 1,4-Diamino anthraquinone

1,4-Diamino anthraquinone synthesis

9synthesis methods
1,4-Diaminoanthraquinone is prepared by hydroxyl replacement from 1,4-dihydroxyanthraquinone via the 2,3-dihydro compound and subsequent oxidation of the intermediate 2,3-dihydro-1,4- diaminoanthraquinone .
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Yield:-

Reaction Conditions:

with sodium hydroxide;hydrazine hydrate in water

Steps:

10 EXAMPLE 10
EXAMPLE 10 14 Parts of 1-amino-4-nitro-anthraquinone, 100 parts of dimethyl sulphoxide, 100 parts of water and 7 parts of hydrazine hydrate are mixed and stirred at 40°. The mixture is gradually heated to 60° over the course of 50 minutes. The pH of the reaction mass is subsequently adjusted to 9-10 by the addition of 2.7 parts of 30% aqueous sodium hydroxide solution. The reaction mass is subsequently stirred at 70° over the course of 4 hours until no starting material can be detected according to chromatography. The reaction mass is poured into 800 parts of water. The precipitate is filtered off, washed with water until the filtrate is neutral and colourless, and then dried. 11 Parts of 1,4-diamino-anthraquinone, having a M.P. of 258°-260°, are obtained.

References:

Sandoz Ltd. US4016182, 1977, A

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