Methanol → 1-Methanesulfonyl-5-methoxy-phenylamine

Participants

Reaction Steps

To a mixture of 1-methanesulfonyl-3-methoxy-5-nitro-benzene (1.5 g, 6.48 mmol), zinc dust (4.3 g, 64.87 mmol), and ammonium chloride (5.2 g, 97.31 mmol) were added methanol (20.32 mL) and water (9.9 mL) at room temperature. After addition of water, the reaction was exothermic. The suspension was stirred for 30 min and the reaction mixture was filtered through the Celite. The filter cake was washed with water and methanol. The filtrate was concentrated to remove methanol and the residue was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to isolate 1-methanesulfonyl-5-methoxy-phenylamine (1.0 g, 76%) as a light yellow solid: ES(+)-HRMS m/e calcd for C8H12NO3S (M+H)+ 202.0533, found 202.0532.

Provenance & Evidence