Hydroxyamine hydrochloride → HCID 18945212, compound

Participants

Reaction Steps

Methyl 3-(2-formylpyrrol-1-yl)benzoate (5.0 g) was added to a mixture of hydroxylamine hydrochloride (1.5 g) and 28% methanolic sodium methoxide (4.2 g) in methanol (50 ml) and the mixture was stirred for 4 hours at ambient temperature. The solvent was removed by concentration and the residue was dissolved in a mixture of ethyl acetate and water. The mixture was adjusted to pH 2 with 6N-hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on silica gel eluting with a mixture of chloroform and ethyl acetate (19:1). The first eluted fractions containing the desired product were collected and evaporated in vacuo and the residue was triturated with a mixture of diisopropyl ether and n-hexane to give methyl 3-[(E)-2-hydroxyiminomethylpyrrol-1-yl]benzoate (Compound A) (0.8 g). The further eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-[(Z)-2-hydroxyiminomethylpyrrol-1-yl]benzoate (Compound B) (1.43 g) as an oil.

Provenance & Evidence