Ammonium Chloride → 5-Amino-1-chloroisoquinoline

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To a 1000 mL 3-neck round-bottomed flask containing 1-chloro-5-nitroisoquinoline (Step 1, 8.200 g, 39.3 mmol) was added Iron powder (11.80 g, 211.2 mmol), while under a flow of inert gas. A 3:1 mixture of EtOH/H2O (240 mL), and NH4Cl (1.19 g, 22.4 mmol) were added. The mixture was heated to 80° C., while stirring under inert atmosphere for 1 hour. The oil bath was removed and the mixture was allowed to cool to ambient temperature. The crude material was filtered through a plug of Celite, and the filtrate was concentrated in-vacuo. Recrystallization from DCM/Hexanes, and further washing the solid with hexanes (3×100 mL) afforded a brown crystalline solid, which was titled product (7.015 g, 39.3 mmol). MS (ESI pos. ion) m/z: 179 (M+H). Calc'd Exact Mass for C9H7N2Cl: 178.5

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