Hydrochloric Acid → 5-[2-(Dimethylamino)ethoxy]pyridine-2-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of the above 5-hydroxypyridin-2-carboxaldehyde (4 g, 0.032 mol), K2CO3 (14 g, 0.097 mol) in THF (100 mL) was heated at 60° C. for 2 h under N2. 2-Dimethylaminoethylchloride was freshly prepared from the corresponding HCl salt (9.4 g, 0.06 mol) to which was added drop-wise 20% NaOH solution (2 equivalent) at 0° C. it was then added drop-wise to the above reaction mixture at 60° C. The reaction mixture was allowed to stir 6 h at the same temperature. Upon completion, the reaction mixture was cooled down to RT, the solid was filtered off and the filtrate was concentrated under vacuum to give expected crude product. It was then purified by column chromatography over silica gel (gradient methanol in chloroform from 0.1% to 2%) to give the desired aldehyde (XVI*), e.g., 5-[2-(dimethylamino)ethoxy]pyridine-2-carboxaldehyde (3.25 g, 51%) as a colorless liquid.

Provenance & Evidence