N-Methylaniline → Butanoic acid, 4-(methylphenylamino)-

Temperature

110 °C

A mixture of N-methylaniline (10 g), ethyl 4-bromobutyrate (13.2 ml) and potassium carbonate (12.7 g) was stirred for 1.5 hour at 110° C. After cooling to room temperature, ethanol (100 ml) and 3N aqueous sodium hydroxide (100 ml) were added to the mixture, and the mixture was stirred for 30 minutes under reflux. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was diluted with water and then washed with ether. The aqueous layer was acidified to pH 4 with concentrated hydrochloric acid and extracted three times with ethyl acetate. The organic layers were collected and extracted twice with 3N hydrochloric acid. The aqueous layers were collected, adjusted to pH 4 by using 20% NaCl aqueous solution, and extracted five times with an ethyl acetate. The combined organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 14.8 g (84%) of the objective compound.

1. temperatureAfter cooling to room temperature
2. stirringthe mixture was stirred for 30 minutes
3. temperatureunder reflux
4. temperatureAfter cooling to room temperature
5. concentrationthe reaction mixture was concentrated under reduced pressure
6. additionthe residue was diluted with water
7. washwashed with ether
8. extractionextracted three times with ethyl acetate
9. customThe organic layers were collected
10. extractionextracted twice with 3N hydrochloric acid
11. customThe aqueous layers were collected
12. extractionextracted five times with an ethyl acetate
13. washThe combined organic layer was washed with water and saturated sodium chloride
14. dry with materialdried over anhydrous sodium sulfate
15. concentrationconcentrated under reduced pressure

ORD record

ord-8667cb695c85482298fa2fa2149fb5ad

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05397781