Methyl iodide → Methyl 2-(methyl(phenyl)amino)acetate

The mixture of N-phenylglycine methyl ester (0.99 g, 6 mmol), potassium carbonate (1.66 g, 12 mmol), and iodomethane (1.28 g, 9 mmol) in acetonitrile (20 mL) was refluxed overnight. The solids were filtered and the filtrate was diluted with water (100 mL), extracted with dichloromethane (4×50 mL). The combined organic extracts were washed with brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane) to afford the title compound (0.82 g, 77%). 1H NMR (400 MHz, CDCl3) δ: 7.24 (m, 2H), 6.75 (m, 1H), 6.67 (m, 2H), 4.07 (s, 2H), 3.71 (s, 3H), 3.06 (s, 3H).

1. temperaturewas refluxed overnight
2. filtrationThe solids were filtered
3. additionthe filtrate was diluted with water (100 mL)
4. extractionextracted with dichloromethane (4×50 mL)
5. washThe combined organic extracts were washed with brine (100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane)

ORD record

ord-20ff1cebb41c42a1ab58c20fe04b0e2d

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07160902B2