Hydroxyamine hydrochloride → HCID 12993705, compound

Participants

Reaction Steps

To a mixture of 3-cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}-2-ethoxymethylenepropan-1,3-dione (3.22 g) and hydroxylamine hydrochloride (0.54 g) in ethanol (15 ml), sodium acetate (0.62 g) was added in several portions while stirring and the mixture was stirred at room temperature for 6 hours. The solvent was distilled off the mixture under reduced pressure and the residue was extracted with ethyl acetate (120 ml), washed with salt water and dried with anhydrous magnesium sulfate. The residue, obtained by distilling off the ethyl acetate, was purified by silica column chromatography (ethyl acetate:n-hexane=1:1) to obtain the objective 5-cyclopropyl-4-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorobenzoyl}isoxazole (2.37 g, 84% yield from 3-cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}propan-1,3-dione. nD20: 1.5929.

Provenance & Evidence