Hydroxyamine hydrochloride → HCID 21834436, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 147 mg (0.612 mmol) of 6-(3-buten-1-yl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine and 215 mg (3.09 mmol) of hydroxylamine hydrochloride in 1.6 mL of 95% ethanol and 0.6 mL of water was heated overnight in a 100° C. oil bath. After cooling to room temperature, the solution was diluted with 25 mL of ethyl ether and washed with 15 mL of 2.5 N aqueous sodium hydroxide followed by 15 mL of saturated aqueous sodium chloride. The aqueous layers were extracted in succession with 25 mL of ethyl ether. The combined ethyl ether layers were dried (sodium sulfate), decanted, and evaporated. Flash column chromatography on 6 g of silica gel eluting with 100 mL of 1:1 ethyl acetate/dichloromethane gave 82 mg (83% yield) of 2-amino-6-(3-buten-1-yl)-4-methylpyridine as a pale yellow oil.

Provenance & Evidence