General procedure for the synthesis of 2-amino-5-chloro-3-methylbenzoic acid from 2-amino-3-methylbenzoic acid: In a 100 mL round-bottomed flask, 20 mL of 2-amino-3-methylbenzoic acid, 50 mL of N,N-dimethylformamide (DMF), and 30 mmol of N-chlorosuccinimide (or N-bromosuccinimide) were added. The mixture was stirred under reflux conditions for 3 hours. After the reaction was completed, the reaction solution was poured into ice water. The pH was adjusted to 6 with dilute hydrochloric acid and then filtered. The resulting solid was washed with a small amount of ethanol to give a gray solid 2-amino-5-halogeno-3-methylbenzoic acid (halogen was chlorine or bromine). The yield was 83%.
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