Hydrochloric Acid → N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

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Reaction Steps

11.4 g (64 mmol) of 2-(pivaloylamino)pyridine was dissolved in 50 mL of tetrahydrofuran, and 100 mL (0.16 mol) of 1.6 M normal-butyllithium was added dropwise thereto at −60° C. The mixture was allowed to react for 3 hours at −10° C. To this reaction mixture, 14 g (0.19 mol) of N,N-dimethylformamide was added dropwise at −60° C., and the reaction liquid was stirred overnight at room temperature. The reaction mixture was poured into ice, and 6 N hydrochloric acid was added thereto to acidify the reaction mixture. Subsequently, potassium carbonate was added to make the reaction mixture alkaline, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, and was dried and concentrated. The residue thus obtained was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:0), and thus 6.57 g (yield 50%) of the title compound was obtained as a pale yellow liquid.

Provenance & Evidence