Sodium hydride → 5-fluoro-N-(4-methoxybutyl)-2-nitroaniline

5-Fluoro-2-nitroaniline (1.0 g) was dissolved in THF (20 ml), sodium hydride (60% in oil, 384 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Methoxybutyl methanesulfonate (1.28 g) was added, and the mixture was heated under reflux with stirring for 15 hr. The reaction mixture was cooled to room temperature and saturated brine was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (30:70) was concentrated under reduced pressure to give the object product (494 mg).

1. temperaturethe mixture was heated
2. temperatureunder reflux
3. stirringwith stirring for 15 hr
4. temperatureThe reaction mixture was cooled to room temperature
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. washa fraction eluted with ethyl acetate-hexane (30:70)
10. concentrationwas concentrated under reduced pressure

ORD record

ord-09f73ebbb4044261af8317f7341b29d0

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045436B2