Hydrochloric Acid → HCID 18546141, compound

Participants

Reaction Steps

To a solution of 5-amino-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (7.10 g) in acetone (200 ml)-water (50 ml) was added dropwise concentrated hydrochloric acid (7.46 g) under ice cooling, and then solution of sodium nitrite (1.83 ) in water (10 ml) was added dropwise. The mixture was stirred for 10 minutes. To the mixture was added a solution of sodium iodide (4.40 g) in water (20 ml) under ice cooling. The mixture was stirred at 15°-20° C. for 2 hours. To the reaction mixture was added water, and the mixture was neutralized with a solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:9, v/v), crystals (6.65 g, 67%) of 5-iodo-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine were obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms. Melting point: 129°-130° C.

Provenance & Evidence