Hydrazine hydrate (1:1) → N6-[3-(N-hydroxyimino)butyl]adenine

Participants

Reaction Steps

0.232 g (1.00 mmol) of N-[3-(N-hydroxyimino)butyl]phthalimide was dissolved in 6 ml of methanol and to the solution was added 60 μl (1.2 mmol) of hydrazine hydrate, followed by being refluxed for 5 hours. The reaction mixture was cooled to room temperature and then, 20 ml of ether was added thereto and the mixture was left to stand at 0° C. for 1 hour to sufficiently precipitate solids. The solids were removed by suction filtration and the filtrate was dried over sodium sulfate and concentrated to 1 ml by an evaporator. This concentrated filtrate was dissolved in 5 ml of isopropanol and to the solution were added 75 mg (0.50 mmol) of 6-chloropurine and 101 μl of ethyldiisopropylamine, followed by being refluxed on an oil bath for 5 hours. The reaction mixture was poured into 20 ml of water and extracted with chloroform (15 ml×5). The extract was dried over magnesium sulfate and the solvent was distilled off. The residue was purified by a thin layer chromatography (silica gel, developing agent: 15% ethanol-chloroform) to give 45.1 mg (yield 22%) of the titled compound as white solids.

Provenance & Evidence