N-Methylaniline → (Methyl-phenyl-amino)-acetic acid ethyl ester

Participants

Reaction Steps

To a solution of bromoethylacetate, 3.3 mL (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.14 g (30.0 mmol) of potassium carbonate and 3.25 mL of N-methylaniline. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using EtOAc/hexanes as eluent and concentrated to dryness to give 4.74 g (82%) of the desired product as a tan oil. MS (ion spray) 194.1 (M+1).

Provenance & Evidence