Hydrochloric Acid → 3,7-Dimethylbenzo[d]isoxazol-5-amine

Participants

Reaction Steps

To a suspension of 3,7-dimethyl-5-nitrobenzo[d]isoxazole (Step 46.5) (50 mg, 0.260 mmol) in acetic acid (1.5 mL) was added dropwise a solution of SnCl2.2H2O (176 mg, 0.781 mmol) in HCl conc (0.316 mL, 10.41 mmol) and the resulting mixture was stirred at RT overnight. The reaction was poured into a cold 4N NaOH solution and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 0-55%) to afford the title product (25 mg, 0.153 mmol, 59% yield) as beige solid. tR: 0.57 min (LC-MS 2); ESI-MS: 163 [M+H]+; Rf=0.23 (hexane/EtOAc 1:1).

Provenance & Evidence