Hydrazine hydrate (1:1) → HCID 54554464, compound

Participants

Reaction Steps

Hydrazine hydrate (696 μl, 716 mg, 14.3 mmol) was added dropwise to a solution of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-phthalimidoethyl)methanesulphonamide (3.76 g, 7.15 mmol) in a mixture of dichloromethane (71 ml) and methanol (5 ml) at room temperature under nitrogen. The mixture was heated at reflux for 4 days and then further methanol (20 ml) was added. After a further 2 days the mixture was allowed to cool and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and this was extracted 3 times with 10% aqueous citric acid. The combined acid extracts were adjusted to pH 9 with solid potassium carbonate and extracted 3 times with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 95:5 dichloromethane:methanol to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-aminoethyl)methanesulphonamide (1.96 g, 69%) as a pale yellow solid.

Provenance & Evidence