1 8-DIAMINO-4 5-DIHYDROXYANTHRAQUINONE synthesis

5synthesis methods

Product Name:1 8-DIAMINO-4 5-DIHYDROXYANTHRAQUINONE
CAS Number:128-94-9
Molecular formula:C14H10N2O4
Molecular Weight:270.24

4,5-Diamino-1,8-dihydroxyanthraquinone is prepared from 1,8-dihydroxy-4,5-dinitroanthraquinone by reduction or by cleavage of the sulfonic acid groups from the corresponding 2,7-disulfonic acid .

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Yield:-

Reaction Conditions:

in ice-water;sulfuric acid;N,N-dimethyl-formamide

Steps:

10 EXAMPLE 10 STR10
EXAMPLE 10 STR10 90 parts of 1,8-dinitroanthraquinone are suspended at room temperature in 1000 parts of dimethyl formamide. To this suspension are then added 45 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 (70% paste) is added in the course of 1 hour to 500 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 300 parts of ice-water, filtered hot. The filter cake is washed neutral with water, affording 44 parts of 1,8-diamino-4,5-dihydroxyanthraquinone. Recrystallisation from dimethyl formamide yields an analytically pure sample with a melting point of about 290° C.

References:

Ciba-Geigy AG US4250102, 1981, A