1-Nitroanthraquinone → 1-Aminoanthraquinone

Participants

Reaction Steps

A 160 ml. electromagnetically stirred autoclave was charged with 2.53 g (0.01 mole) of 1-nitroanthraquinone (roughly purified product with no impurity detected by thin-layer chromatography), 52 g (0.05 mole) of a 4% aqueous solution of sodium hydroxide and 0.07 g of Raney nickel. The 1-nitroanthraquinone was hydrogenated with stirring at room temperature and a pressure of 6 to 3 Kg/cm2. G. The reaction proceeded smoothly, and stopped in 6 hours with the absorption of 0.04 mole of hydrogen. The inside of the autoclave was purged with nitrogen, and the reaction mixture was filtered in an atmosphere of nitrogen to separate the catalyst. The filtrate was oxidized with air at 20° to 30°C. for 1 hour with stirring to afford 2.1 g of 1-aminoanthraquinone having a purity of 97% by weight in a yield of 94% of theory. By a thin layer chromatographic analysis, no impurity was detected in the resulting product.

Provenance & Evidence