Example 129B Synthesis of 6-amino-1-indanone: To a solution of Example 129A (19.68 g, 111 mmol) in ethanol (111 mL) was sequentially added iron powder (43.0 g, 770 mmol) and solid ammonium chloride (3.70 g, 69.2 mmol). The resulting suspension was stirred at 90 °C for 1 h. The reaction was cooled to room temperature upon completion. The reaction mixture was diluted with brine and extracted with ether (4 x 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give a mixture of 6-amino-1-indanone and 4-amino-1-indanone (14.20 g, 87% yield, 6:1 ratio).1H NMR (300 MHz, DMSO-d6) data: 6-amino-1-indanone: δ 7.21 (d, 1H), 6.92 (dd, 1H), and 6.75 (d, 1H), 5.27 (br s, 2H), 2.90 (t, 2H), 2.54 (m, 2H); 4-amino-1-indanone: δ 7.10 (t, 1H), 6.81 (m, 2H), 2.80 (m, 2H), 2.59 (m, 2H).
