Under argon protection and magnetic stirring conditions, 1-nitropyrene (1.00 g, 4.0 mmol) was dissolved in 60 mL of ethyl acetate with tin(II) chloride dihydrate (4.35 g, 19.2 mmol) in a 250 mL three-necked round-bottomed flask. The reaction mixture was heated to reflux for 6 hours. After the reaction was completed, it was cooled to room temperature and the pH was adjusted to 8.0 by slowly adding 20% (m/v) aqueous sodium carbonate solution and continued stirring for 1 hour. The reaction mixture was extracted three times with ethyl acetate, the organic phases were combined and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give a light green solid product 1-aminopyrene 0.80 g (90% yield). The product was characterized by the following data: melting point 115-116 °C (literature value: 115-117 °C); IR (KBr) νmax/cm?1: 3345-3387 (N-H stretching vibration), 3036 (aromatic C-H stretching vibration), 1623-1512 (C=C stretching vibration); 1H NMR (400 MHz, DMSO-d?) δ: 8.24 (d, 1H, J=9.4 Hz, Ar-H), 7.97 (d, 2H, J=7.8 Hz, Ar-H), 7.94 (d, 1H, J=7.8 Hz, Ar-H), 7.89 (d, 1H, J=9.0 Hz, Ar-H), 7.86 (d, 1H, J=8.6 Hz, Ar-H), 7.85 (t, 1H, J=7.6 Hz, Ar-H), 7.69 (d, 1H, J=8.6 Hz, Ar-H), 7.34 (d, 1H, J=8.2 Hz, Ar-H), 6.33 (s, 2H, NH?).
