Methanol → Methyl 3-(4-aminophenyl)propanoate

Under ice-cooling, thionyl chloride (15 mL, 206 mmol) was added dropwise to methanol (60 mL), and the mixture was stirred for 10 min. 3-(4-Aminophenyl)propanoic acid (10.1 g, 61.1 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hr. The solvent and excess thionyl chloride were evaporated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate were added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound (10.9 g, yield 99%) as pale-brown prism crystals.

1. temperatureUnder ice-cooling
2. stirringthe mixture was stirred at room temperature for 18 hr
3. customThe solvent and excess thionyl chloride were evaporated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate
4. additionwere added
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. concentrationconcentrated under reduced pressure
9. washThe obtained solid was washed with hexane

ORD-Eintrag

ord-41aef0ea374d430f88bda8905e5d0118

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07786165B2