Three phenolic derivatives of 2-aminoanthracene have been prepared as their diacetyl derivatives by Bucherer-type amination of appropriately substituted anthracenes. Since many aromatic compounds are metabolized to phenolic products' in mammalian systems by oxygenases such as cytochrome P-450, the need for phenols of the potent carcinogen 2-aminoanthracene in carcinogenesis research was evident. We report here the synthesis of the acetylated derivatives' of Z-amino-5-hydroxyanthracene A, 2-amino-6-hydroxyanthracene 2, and 2-amino-8_hydroxyanthracene, 3. The synthetic strategy involved preparation of appropyiately substituted dihydroxyor metFoxy-hydroxy-g,lO-anthraquinones, reduction of these compounds to the corresponding anthracenes, and amination under Bucherer-type conditions to afford the aminohydroxyanthracene derivatives. For compound: the starting dihydroxyanthraouinone was commercially available as anthraflavic acid (2,6-dihydroxy-9,10-anthraquinone) 4. Reduction by the two step method of Clarke and Johnson3 and acetylation of the product gave ?,6,-diacetoxyanthracene, i (42%) mp 263-265.5"C (lit3, mp 265-268Β°C). Heating this symmetrical product in a sealed tube containing concentrated ammonium hydroxide and sodium bisulfite for 1 h at 135Β°C gave a product that, after acetylation and chromatography, yielded 2-acetylamino-6acetoxyanthracene p mp 257-9Β°C (dec).4