5-CHLORO-2-[(CHLOROACETYL)AMINO]BENZOIC ACID synthesis

Yield:14422-50-5 96%

Reaction Conditions:

in toluene; for 1 h;Reflux;

Steps:

72.i

(i) 5-Chloro-2-[(chloroacetyl)amino]benzoic acid 3.0 g (17.5 mmol) of 2-amino-5-chlorobenzoic acid and 3.95 g (35.0 mmol) of chloroacetyl chloride were heated under reflux in 60 mL of toluene for 1 hour. Thereafter, the solvent was distilled off under reduced pressure, and H₂O was added to the resulting residue. Solids were collected by filtration to give 4.15 g of 5-chloro-2-[(chloroacetyl)amino]benzoic acid (yield: 96%). ¹H-NMR (DMSO-d₆) δ: 4.48 (2H, s), 7.70 (1H, dd, J=9.0, 2.6 Hz), 7.96 (1H, d, J=2.6 Hz), 8.55 (1H, d, J=9.0 Hz), 11.77 (1H, s), 14.08 (1H, brs).

References:

US2012/22080,2012,A1 Location in patent:Page/Page column 67