Ethyl chloroformate → 3-(3,4-Dimethoxyphenyl)propanamide

Temperature

-15 °C

To a stirred solution of 3-(3,4-dimethoxy-phenyl)-propionic acid (10.0 g, 47.56 mmol) in dry THF (175 ml), under nitrogen, was added TEA (7.3 ml, 52.44 mmol), and the resulting mixture was cooled to −10° C. before ethyl chloroformate (5 ml, 52.47 mmol) was added dropwise. After stirring at −10° C. (20 min), ammonium hydroxide (25% in water, 105 ml) in THF (105 ml) was added and the mixture was stirred at −15° C. for 30 min and then at RT for 1.5 h. The reaction mixture was concentrated in vacuo, extracted three times with CH2Cl2 and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give the title compound (9.73 g, 46.50 mmol, 97%) as a colorless solid. No further purification of the crude amide was necessary.

1. additionwas added dropwise
2. additionwas added
3. waitat RT for 1.5 h
4. concentrationThe reaction mixture was concentrated in vacuo
5. extractionextracted three times with CH2Cl2
6. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
7. dry with materialThe organic phase was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-9f2c9c174f4749a7ab6f6ca705a270b4

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192950B2