2-Chloro-N-(2-methoxy-5-nitro-phenyl)-acetamide synthesis

Yield:58795-63-4 97%

Reaction Conditions:

with pyridine in dichloromethane at 0 - 20; for 12 h;

Steps:

41A 2-chloro-N-(2-methoxy-5-nitrophenyl)acetamide

To a solution of 2-methoxy-5-nitroaniline (10.00 g, 59.5 mmol) and pyridine (5.1 mL, 62.4 mmol, 1.05 equiv) in CH2CI2 (175 mL) at 0 °C was added chloroacetyl chloride (4.97 mL, 62.4 mmol, 1.05 equiv) dropwise. The resulting mixture was warmed to room temperature, and was stirred at that temperature for 12 h. The resulting solution was concentrated under reduced pressure. The remaining solids were triturated with ethanol, filtered, washed with ethanol, followed by water, followed by ethanol, and dried at 50 °C under reduced pressure to give 2-chloro-N-(2-methoxy-5- nitrophenyl)acetamide (14.1 g, 97%).¹H-NM (400 MHz, DMSO-d₆): δ [ppm] = 3.98 (s, 3H), 4.41 (s, 2H), 7.27 (d, J=9.1 Hz, 1H), 8.04 (dd, J=2.8, 9.1 Hz, 1H), 8.95 (d, J=2.8 Hz, 1H), 9.85 (s, 1H).LC-MS (Method 3): R_t= 0.95 min; MS (ESIpos): m/z = 245 ([M+H]⁺, 100%); MS (ESIneg): m/z = 243 ([M-H]-, 100%).

References:

WO2014/147182,2014,A2 Location in patent:Page/Page column 103; 104