(4-Chloro-benzoylamino)-acetic acid

59893-99-1

13450-77-6

In a 500 mL round bottom flask, methyl 2-(4-chlorobenzoylamino)acetate (20 g, 88.1 mmol) was dissolved in a solvent mixture of THF (100 mL), methanol (100 mL) and water (100 mL) and lithium hydroxide monohydrate (18.5 g, 441 mmol) was added with stirring. The reaction mixture was stirred continuously for 12 hours at room temperature. After the completion of the reaction was monitored by TLC, the reaction mixture was concentrated under reduced pressure. The resulting residue was washed with EtOAc, subsequently diluted with cold water and acidified with 1N HCl solution to pH about 5. The solid product was collected by filtration and dried under reduced pressure to afford the target compound 2-(4-chlorobenzoylamino)acetic acid (14.21 g, 75.6% yield). The product was characterized by the following data: 1H NMR (300 MHz, DMSO-d6): δ 12.7 (brs, 1H), 8.93 (t, J = 5.7 Hz, 1H), 7.88-7.84 (m, 2H), 7.54 (d, J = 8.7 Hz, 2H), 3.90 (d, J = 6.3 Hz, 2H). lCMS (ESI+, m/ z): 214.0, 216.0 (M + H)+.