Ethyl bromoacetate → [(3-Chloro-phenyl)-methyl-amino]-acetic acid ethyl ester

To a solution of 3-chloro-N-methylaniline (0.50 g, 3.35 mmol) in ethanol (7 ml) were added sodium carbonate (0.53 g, 5.03 mmol) and ethyl bromoacetate (0.42 ml, 3.69 mmol). The resulting suspension was stirred at room temperature for 1 hour and was then heated at 100° C. for 15 min under microwave irradiation. The mixture was then cooled to room temperature, diluted with ether, and filtered. The filtrate was washed with 1 M aqueous hydrochloric acid, the phases separated, and the aqueous phase extracted with ether. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30) to yield a brown oil (0.49 g, 64%); MS (ISP): 230.3, 228.1 ([M+H]+.).

1. temperaturewas then heated at 100° C. for 15 min under microwave irradiation
2. temperatureThe mixture was then cooled to room temperature
3. filtrationfiltered
4. washThe filtrate was washed with 1 M aqueous hydrochloric acid
5. customthe phases separated
6. extractionthe aqueous phase extracted with ether
7. dry with materialThe combined organic extracts were dried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30)

ORD record

ord-d44f30d20fe34b8a94fc1f82d97dc80c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652055B2