Water → Cyclopropanecarboxylic acid acetyl-(3-iodo-phenyl)-amide

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Reaction Steps

In analogy to Example 13ap), from N-benzyl-5-bromo-isatin (G.Tacconi et al., J. Prakt. Chem. 315, 339 (1973)) there is obtained the corresponding N-benzyl-5-bromo-isatin oxime as a yellow solid. Yield: 94%. Mass spectrum: peaks inter alia at 330 (M+, 17%); 285 (14%), 91 (100%). 13ar) 1.36 g of N-acetyl-3-iodo-aniline are dissolved in 25 ml of methylene chloride and treated with 61 mg of 4-dimethylamino-pyridine. A solution of 5.25 ml of cyclopropanecarbonyl chloride in 7 ml of methylene chloride is added dropwise to this solution. The mixture is stirred at room temperature overnight, then poured into 100 ml of water and made weakly acid with a few drops of dil. hydrochloric acid. Extraction with ethyl acetate and chromatography on silica gel with ethyl acetate gives 1.85 g of cyclopropanecarboxylic acid acetyl-(3-iodo-phenyl)-amide as a yellowish oil which solidifies in time. Yield: 92%. Mass spectrum: peaks inter alia at 329 (M+, 8%); 287 (58%), 69 (100%).

Provenance & Evidence