Hydrochloric Acid → 5-Iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (10.0 g), conc. HCl (8.47 ml) and acetone (100 ml), a solution of sodium nitrite (NaNO2) (2.46 g) in water (10 ml) was added dropwise at a temperature of under 10° C. After mixture was stirred at 10° C. for 30 minutes, a solution of potassium iodide (KI) (2.46 g) in water (10 ml) was added dropwise to the mixture. The reaction mixture was stirred at 30° to 35° C. for 1 hour and then at 35° to 40° C. for 1 hour, after which it was concentrated under reduced pressure. The residue was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residual oily substance was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:3, v/v), 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (7.22 g, 52%) was obtained, which was then recrystallized from ethyl acetate-hexane to yield a colorless crystal.

Provenance & Evidence