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

Temperature

0 °C

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.

1. stirringAfter stirring for 15 minutes
2. temperaturethe reaction mixture was then warmed up to ambient temperature
3. stirringstirred overnight
4. filtrationThe precipitate was collected via suction filtration
5. concentrationconcentrated under vacuum
6. customto remove the water
7. customFinally, the solid was recrystallized from 2-propanol

ORD record

ord-7a0b59e8383f4d659c07f808af1e0d51

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019147B1