Anthranilic Acid → HCID 11961502, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of 2,4-dichloro-5-nitropyrimidine (0.53 g, 2.75 mmol) in THF (2 mL) was added a solution of anthranilic acid (0.37 g, 2.50 mmol) and N,N-diisopropylethylamine (0.5 mL, 3.0 mmol) in THF (2.0 mL). The reaction was stirred for 2.0 hours. The reaction was then poured onto ice and allowed to warm to room temperature then was filtered. The isolated solid was dried under vacuum, then recrystallized from hot ethyl acetate and cold hexane to give 2-[(2-chloro-5-nitropyrimidin-4-yl)amino]benzoic acid (307 mg, 42%) as a yellow solid. 1H NMR (DMSO-d6/D2O): δ 9.20 (s, 1H), 8.36 (d, 1H), 8.07 (d, 1 H), 7.70 (t, 1 H), 7.37 (t, 1 H). MS m/z 294 (M+1).

Provenance & Evidence