Chlorosuccinimide → 2-Amino-5-chloro-3-methylbenzoic acid

Temperature

100 °C

To a solution of 2-amino-3-methylbenzoic acid (Aldrich, 15.0 g, 99.2 mmol) in N,N-dimethylformamide (50 mL) was added N-chlorosuccinimide (13.3 g, 99.2 mmol) and the reaction mixture was heated to 100° C. for 30 minutes. The heat was removed and the reaction mixture was cooled to room temperature and allowed to stand overnight. The reaction mixture was then slowly poured into ice water (250 mL) to precipitate a white solid. The solid was filtered and washed four times with water and then taken up in ethyl acetate (900 mL). The ethyl acetate solution was dried over magnesium sulfate, evaporated under reduced pressure and the residual solid was washed with ether to afford the desired intermediate as a white solid (13.9 g).

1. customThe heat was removed
2. temperaturethe reaction mixture was cooled to room temperature
3. additionThe reaction mixture was then slowly poured into ice water (250 mL)
4. customto precipitate a white solid
5. filtrationThe solid was filtered
6. washwashed four times with water
7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
8. customevaporated under reduced pressure
9. washthe residual solid was washed with ether

ORD record

ord-e87a9c4fb20544d9b5b50750ead73e7f

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07339057B2