1,1-Dimethoxyethyl(dimethyl)amine → 3-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehyde

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Reaction Conditions

Reaction Steps

A mixture of 3-[1,3]dioxolan-2-yl-benzamide (2.3 g) and dimethylacetamide dimethylacetal (4 g) was heated under reflux for 1 hour and then evaporated to dryness. The oily residue was dissolved in dioxane (20 mL) and hydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added and the mixture was heated at 90° C. for 2 hours. After evaporation, the residue was dissolved in toluene (100 mL) and a 1N hydrochloric acid solution (50 mL) was added and the mixture was stirred at reflux for 2 hours. After cooling at room temperature the organic phase was decanted, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.3 g) as a white solid.

Provenance & Evidence