Hydrochloric Acid → Acetamide, 2-(hydroxyimino)-N-phenyl-

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Chloral hydrate (5.0 g) and Na2SO4 (35.0 g) were dissolved in water (70 mL) in a 300 mL beaker and warmed to 35° C. A warm solution of the appropriate commercial aniline derivative Ia-d (27.6 mmol) in water (20 mL) and aqueous solution of conc. HCl (3 mL) was added (a white precipitate of the amine sulfate was formed), followed by a warm solution of hydroxylamine hydrochloride (6.1 g) in water (27.5 mL). The mixture was stirred by hand and heated on a hot plate (a thick paste formed at 75-70° C.) at 80-90° C. for 2 h, then allowed to cool for 1 h, by which time the temperature had fallen to 50° C., and filtered. The pale cream product was washed by stirring with water (100 mL) and filtered. Drying overnight at 40° C. gave the corresponding isonitrosoacetanilide IIa-d.

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