1-Nitroanthraquinone → 1-Aminoanthraquinone

Participants

Reaction Steps

300 Parts by weight of anisole are mixed with 27 parts of (97 percent) 1-nitroanthraquinone and 0.2 parts by weight of a palladium/charcoal catalyst (5 percent of Pd on active charcoal) and heated to 130° in an autoclave. At this temperature, hydrogen is blown through until the rate of up-take of the hydrogen has fallen to 10 percent of the original value. At this stage, about 2 percent of overhydrogenated product is present (ascertained by TLC). After interruption of the hydrogen supply, at 130°, 0.4 parts by weight of 1-hydroxylaminoanthraquinone are added and stirring is effected for 30 minutes. The catalyst is separated off at the upper temperature, the filtrate is concentrated and cooled and the 1-aminoanthraquinone is filtered off. No nuclear hydrogenated 1-aminoanthraquinone is present in the mother liquor. 23 Parts of 97 percent pure 1-aminoanthraquinone is obtained.

Provenance & Evidence