Hydrochloric Acid → (2E)-N-(4-bromo-3-methoxyphenyl)-2-hydroxyiminoacetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-3-(methyloxy)aniline (50 g, 247 mmol), HCl (100 mL) and dioxane (150 mL) in H2O (500 mL) was stirred at 50° C. 2,2,2-Trichloro-1,1-ethanediol (81.7 g, 494 mmol), Na2SO4 (526 g, 3705 mmol) and H2O (1 L) were added to the mixture followed by NH2OH.HCl (103 g, 1482 mmol in 100 mL of H2O). The mixture was stirred at 80° C. for 1 h, cooled to room temperature, filtered and washed with H2O to yield (2E)-N-[4-bromo-3-(methyloxy)phenyl]-2-(hydroxyimino)ethanamide (75 g) as a yellow solid. MS (m/z) 273 (M+H+).

Provenance & Evidence