General procedure for the synthesis of 4-(2-aminoethyl)-2-methoxyphenol hydrochloride from 2-methoxy-4-(2-nitroethyl)phenol: 2-methoxy-4-(2-nitroethyl)phenol (8 g, 40.6 mmol), ethyl acetate, and concentrated hydrochloric acid were added to a reaction flask and heated to 70 °C. Activated zinc powder (35.0 g, 546.5 mmol) was slowly added under vigorous stirring, followed by slow cooling to 50 °C. After the addition of zinc powder, the reaction was continued for 3 h, during which vigorous stirring was maintained and the reaction progress was monitored by TLC. After completion of the reaction, it was cooled to room temperature and filtered to remove the excess zinc powder. The filtrate was dried with anhydrous sodium sulfate, and the filtrate was collected after filtration again and concentrated to give the oily product 4-(2-aminoethyl)-2-methoxyphenol (6.7 g, 40.0 mmol). To the oily product was added 4 M hydrochloric acid-methanol solution, shaken well and then frozen at -20 °C for 2 hours. Filtration gave the precipitated solid, 3-methoxy-4-hydroxyphenethylamine hydrochloride (6 g, yield about 72%).
