Hydrochloric Acid → 2-Hexyloxy-4-nitroaniline

Participants

Reaction Steps

General Procedure for the Preparation of the base compound and Compounds 9-16. NaH (95% powder, 0.265 g, 10.5 mmol, 3.5 equiv) was added to a solution of alkyl instituted 2-amino-5-nitrophenol (3.0 mmol) in anhydrous DMF (8 mL) at room temperature. After being stirred at the same temperature for 30 min, MsCl (1.031 g, 9.0 mmol, 3 equiv) was added to the mixture, and the stirring was continued overnight at room temperature. H2O was added to the mixture, and then it was neutralized with 5 N HCl until pH=1-2. The intermediate precipitated as a yellow solid. It was collected by filtration and washed with H2O, which was used to the next reaction without further purification. The intermediate was added to a 3 N NaOH aq solution and was stirred at 80-90° C. overnight. After being cooled, it was neutralized with 5 N HCl until pH=1-2. The precipitated solid was collected and washed with H2O and cold ether to provide the desired product, and then it was recrystallized from ethyl acetate/hexane.

Provenance & Evidence