Water → 5-(2-Methoxyethoxy)-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

4-Amino-3-nitrophenol (58.53 g, 379.7 mMol) was dissolved in 600 mL of anhydrous DMF under an atmosphere of dry N2 and the solution was mechanically stirred. The reaction mixture was then cooled to 0° C. and to this mixture was added CS2CO3 (177.4 g, 455.7 mMol), sodium iodide (5.7 g, 37.9 mMol) and 2-bromoethyl methyl ether (39.3 mL, 417.7 mMol). After stirring for 15 minutes, the reaction mixture was then warmed up to ambient temperature and then stirred overnight. The reaction mixture is then poured into 6 L of water. The precipitate was collected via suction filtration. The wet precipitate was taken up in toluene and then concentrated under vacuum to remove the water. Finally, the solid was recrystallized from 2-propanol to give 57.93 g of 5-(2-Methoxy-ethoxy)-2-nitro-phenylamine 42A as an orange solid. A second crop of 12.5 g of compound 42A was also obtained.

Provenance & Evidence