Hydrochloric Acid → 2-Chloro-3,4-dimethoxyphenethylamine

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Reaction Steps

To tetrahydrofuran (THF) (60 mL) was added lithium aluminum hydride (1.822 g, 48.0 mmol) at 0° C. and aluminium chloride (6.40 g, 48.0 mmol) in tetrahydrofuran (THF) (80 mL) was added via syringe. The solution of (E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (5.85 g, 24 mmol) in tetrahydrofuran (THF) (100 mL) was added via addition funnel over 40 min. Stirred at rt for 16 h. Water (8 ml) was added dropwise followed by 5N hydrochloric acid (60 ml). The mixture was washed with ether (2×200 mL) and the aqueous phase was made basic with 6N sodium hydroxide. The aqueous layer was extracted with ether (3×200 mL). Dried over magnesium sulfate, evaporated to give 2-(2-chloro-3,4-dimethoxyphenyl)ethanamine (2.85 g, 13.21 mmol, 55.1% yield). LCMS (M+H)+: 216.0

Provenance & Evidence