Ethoxalyl chloride → Ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate

Participants

Reaction Steps

To a solution of 2-amino-4-chlorobenzamide (393 mg, 2.30 mmol) and DIEA (0.60 mL, 3.45 mmol) in THF (15 mL) at 0° C. was added ethyl chlorooxoacetate (0.28 mL, 2.53 mmol). The solution was allowed to warm to rt and stir for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-50% EtOAc/hexanes to afford ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate as a solid (545 mg, 88%). 1H NMR (300 MHz, DMSO-d6) δ 1.32 (t, J=6.97 Hz, 3 H), 4.31 (q, J=6.97 Hz, 2 H), 7.34 (d, J=8.48 Hz, 1 H), 7.86-8.03 (m, 2 H), 8.44 (br s, 1 H), 8.62 (s, 1 H), 13.24 (s, 1 H)

Provenance & Evidence