Hydroxylamine → HCID 86678191, compound

Participants

Reaction Steps

In ethanol (5 mL) was dissolved 5-(diethoxymethyl)picolinonitrile (230 mg, 1.12 mmol) obtained in Step 1. A 50% aqueous hydroxylamine solution (0.368 g, 5.58 mmol) was added and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The resulting white solid was dissolved in pyridine (5 mL). Acetyl chloride (0.396 mL, 5.58 mmol) was added and the mixture was stirred at 100° C. for 12 hours. The solvent in the reaction mixture was evaporated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 6-(5-methyl-1,2,4-oxadiazol-3-yl)nicotinaldehyde (200 mg, 95% yield).

Provenance & Evidence