Aniline → HCID 564817, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-chloro-3-oxopropanoate (2.0 g, 14.7 mmol) in dry DCM (100 ml) was added aniline (2.68 g, 3.6 mmol) and the reaction mixture was stirred at 0° C. for 1 hr, evaporated then dissolved in EtOAc, washed with dilute HCl, NaHCO3, and brine. The organic phase was collected, dried over sodium sulfate, filtered and the solvent was evaporated to afford methyl 3-oxo-3-(phenylamino)propanoate as a brown oil which was used without further purification (2.8 g, 100%, crude). To a solution of this material (2.8 g, 14.5 mmol) in THF (40 ml) and water (20 ml) was added NaOH (1.16 g, 29 mmol) and the reaction mixture was stirred overnight, evaporated (to remove the THF) and then extracted with Et2O. The aqueous phase was acidified to pH 1 and extracted with EtOAc. The extract was dried over Na2SO4, filtered and evaporated to afford the title compound 1 as a brown solid, which was used without further purification (2.0 g, 77% yield). MS (m/z): 18.0 (100%) (M+H), 202.0 (44%) (M+Na).

Provenance & Evidence