9-Nitroanthracene → 9-Aminoanthracene

Beteiligte Stoffe

Reaktionsschritte

To a solution of tin chloride (25.4 g, 134 mmol) in concentrated hydrochloric acid (HCl, 210 mL) was added dropwise a solution of 9-nitroanthracene (10.0 g, 44.8 mmol) in acetic acid (420 mL), and the mixture was heated to reflux for 1 hour. The mixture was cooled to room temperature and filtered. The residue was treated with an aqueous solution of sodium hydroxide (NaOH, 1 N, 300 mL) and extracted with dichloromethane (CH2Cl2). The organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give anthracen-9-yl-amine as brown crystals (6.41 g, 74% yield). 1H NMR (CDCl3) δ 8.00-7.95 (4H, m), 7.91 (1H, s), 7.47-7.42 (4H, m), 4.89 (2H, br-s).

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