Benzo[d]isoxazol-5-ylaMine

39835-28-4

239097-74-6

GENERAL STEPS: To a 12M HCl (0.5 mL) solution of SnCl4 (1.828 g, 7.02 mmol) under stirring was added 5-nitro-1,2-benzisoxazole (140 mg, 0.86 mmol) in a single addition at 0 °C. After a few minutes of reaction, a 12M HCl (0.5 mL) solution of SnCl2-2H2O (792 mg, 3.51 mmol) was added slowly and dropwise at 0 °C, followed by the addition of 12M HCl (1.0 mL). The reaction mixture was brought to room temperature and stirred continuously for 3 hours. Upon completion of the reaction, the reaction mixture was extracted with Et2O. The aqueous phase was adjusted to pH ~8 with saturated NaHCO3 solution and subsequently extracted with EtOAc. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated, and dried in vacuum to give 1,2-benzisoxazol-5-amine as a colorless solid (110 mg, 95% yield). The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.54 (s, 1H), 7.42 (d, J=8.4 Hz, 1H), 6.94 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.91 (d, J=2.0 Hz, 1H). es-MS m/z: 135.1 [M+H]+. lc-MS analysis Shows purity of 90% (214 nm), retention time tR = 1.32 min.