An improved synthesis of isonitrosoacetanilides

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8719-8721

  Rewcastle, Gordon W ^a   Sutherland, Hamish S ^a   Weir, Claudette A ^a   Blackburn, Adrian G ^a   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Aniline; Isatin; Isonitrosoacetanilide

Indexed keywords

ACETANILIDE DERIVATIVE; ANILINE DERIVATIVE; CHLORIDE; HYDROXYLAMINE; NITROSO DERIVATIVE;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; PHYSICAL CHEMISTRY; SYNTHESIS;

EID: 27744524134     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.046     Document Type: Article

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15. 3).
16. 11 (1.0 g, 5.2 mmol) in dichloromethane (5 mL) was added dropwise. The mixture was removed from the cooling bath and allowed to warm to room temperature. When the complete consumption of the aniline 1 was confirmed by TLC, the solid was removed by filtration, washed well with dichloromethane, and the filtrate was concentrated. Hydroxylamine hydrochloride (1.4 g, 20 mmol) was dissolved in a mixture of ethanol (10 mL) and water (5 mL), and the solution was then added to the crude diacetates 4. The mixture was heated under reflux for 2 h, cooled to room temperature, and concentrated on a rotary evaporator until precipitation commenced. Water was then added to precipitate further product. The solid isonitrosoacetanilide 2 was collected by filtration and washed with water. Purification was by recrystallization or reprecipitation from 5% aqueous NaOH solution with acetic acid.
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