Hydrazine hydrate (1:1) → HCID 21825589, compound

Participants

Reaction Steps

A solution of 15 (2.46 g, 0.01 mol) in methanol (50 ml) and 5% palladium-on-carbon catalyst (500 mg) was stirred at room temperature while a solution of 99% hydrazine hydrate in methanol (1:3, v/v) was added dropwise until evolution of nitrogen ceased. The catalyst was removed by filtration through Celite and the solvent was removed by evaporation in vacuo to give 2.30 g of syrup. The syrup was dissolved in methanol and absorbed on 5 g of silica gel. The methanol was removed and the mixture was added to a dry packed silica gel column (2.5 × 28 cm). The column was eluted with chloroform (0.2 liter), chloroform-ethyl acetate (1:1, 0.2 liter), ethyl acetate (0.2 liter), and ethyl acetate-methanol (9:1, 0.5 liter); 20 ml fractions were collected. Fractions 30-35 provided 2.0 g (93%) of 17 as a syrup: nmr (DMSO-d6) δ 5.62 (d, 1, J1',2' 4.0 Hz, 1'--H), 7.03 (s, 1, 5--H).

Provenance & Evidence