Hydrochloric Acid → 3-Chloro-4-morpholinoaniline

Participants

Reaction Conditions

Reaction Steps

To a mixture of concentrated hydrochloric acid (1.0 mL) and water (50 mL) was added iron powder (7.55 g, 135 mmol) in one portion and the mixture was stirred at 65° C. for 15 min. The aqueous layer of the mixture was poured out and a solution of 4-(2-chloro-4-nitrophenyl)morpholine (3.28 g, 13.5 mmol) in MeOH (50 mL) was added to the above processed iron powder. The mixture was acidified to pH 3 with hydrochloric acid and stirred further at 65° C. for 45 min. The mixture was then cooled to rt, adjusted to pH 10 with Et3N and filtered and the filtrate was concentrated in vacuo. The residue was dissolved in DCM (150 mL) and the solution was washed with water (100 mL×3) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a white solid (2.05 g, 71%).

Provenance & Evidence