A mild and eco-friendly one-pot, two-step procedure has been developed for the synthesis of 2-hydroxy-N-arylacetamides from 2-chloro-N-arylacetamides. The procedure overcomes the cleavage of the amide linkage in 2-chloroacetamides, which is usually observed under reflux conditions with the hydroxide when the nucleophilic substitution of the halide is attempted. The reactions were performed by refluxing 2-chloro-N-arylacetamides with Cu(OAc)2 and DIPEA in the ethanol medium to facilitate an acetate exchange with the halogen. Subsequently, by the addition of ethanolic KOH solution to the same reaction flask, the ester linkage was selectively cleaved in the presence of the amide, taking advantage of the difference in electrophilicity. The procedure afforded good yields of the desired products, which are valuable intermediates for several biologically active molecules, in a short reaction time with ease of isolation. The experimental conditions employed are simple and offer the possibility of scaling up to higher quantities.

中文翻译：

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由 2-氯-N-芳基乙酰胺一锅温和环保合成 2-羟基-芳基乙酰胺

开发了一种温和且环保的一锅两步程序，用于从 2-氯-N-芳基乙酰胺合成 2-羟基-N-芳基乙酰胺。该方法克服了 2-氯乙酰胺中酰胺键的断裂，当尝试卤化物的亲核取代时，通常在氢氧化物回流条件下观察到这种断裂。该反应通过将 2-氯-N-芳基乙酰胺与 Cu(OAc)2 和 DIPEA 在乙醇介质中回流以促进乙酸酯与卤素的交换来进行。随后，通过将乙醇 KOH 溶液添加到同一反应烧瓶中，利用亲电性的差异，在酰胺存在的情况下选择性地裂解酯键。该程序在很短的反应时间内提供了所需产物的良好收率，这些产物是几种生物活性分子的有价值的中间体，并且易于分离。所采用的实验条件很简单，并且提供了扩大到更高数量的可能性。