Hydroxyamine hydrochloride → 1-(2,6-dichloro-3-methylphenyl)-3-hydroxyiminoindol-2-one

Participants

Reaction Steps

A solution of 1-(2,6-dichloro-3-methylphenyl)-1H-indole-2,3-dione (0.3 g) and hydroxylamine hydrochloride (0.07 g) in pyridine (2 ml) is stirred at room temperature for 20 minutes. The reaction mixture is diluted with ethyl acetate (20 ml) and washed with 1 N HCl (2×100 ml). The organic layer is dried (MgSO4) and evaporated. Flash chromatography (silica, CH2Cl2) followed by recrystallization from isopropyl ether affords 1-(2,6-dichloro-3-methylphenyl)-1H-indole-2,3-dione 3-oxime (256 mg, 80%), mp 190°-191° C.

Provenance & Evidence