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 (MgSO4) and evaporated under reduced pressure, and the residual solid was washed with ether to afford the desired intermediate as a white solid, 13.9 g (75.4% yield).

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 (MgSO4)
8. customevaporated under reduced pressure
9. washthe residual solid was washed with ether

ORD record

ord-1ae2baa593694acd8f8653c196f4bcf8

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528260B2