Phenylacetic Acid → N-Methyl-2-phenylacetamide

Phenylacetic acid (10 g, 73.5 mmol) and methanol (60 ml) were added to a 250 ml three-necked flask, followed by addition of 10 drops concentrated sulphuric acid. The resulting solution was heated to reflux for 2 hours. Then, the solution was cooled to room temperature, followed by adding 25-30% aqueous solution of methylamine (50 ml, approximately 403 mmol), and heated to reflux for another 3 hours. After the reaction was completed, it was cooled to room temperature. Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added thereinto, and then the mixture was extracted with ethyl acetate (3×80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield 10.1 g of N-methyl phenylacetamide (white solid, yield: 91.8%).

1. temperatureThe resulting solution was heated
2. temperatureto reflux for 2 hours
3. temperatureheated
4. temperatureto reflux for another 3 hours
5. temperatureit was cooled to room temperature
6. customMost of the solvent was removed by rotary vacuum evaporation, 30 ml of water
7. additionwas added
8. extractionthe mixture was extracted with ethyl acetate (3×80 ml)
9. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
10. filtrationfiltrated
11. concentrationconcentrated under reduced pressure

ORD record

ord-5194747d16404dc8a43b67fe9d21f091

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822519B2