Hydrazine hydrate (1:1) → HCID 21825590, compound

Participants

Reaction Steps

A solution of 16 (1.23 g, 0.005 mol) in methanol (25 ml) and 5% palladium-on-carbon catalyst (250 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. The product was crystallized from ethyl acetate-methanol (3:1) to give 1.0 g (92%) of 18, m.p. 102°-104°. The nmr spectrum indicated the presence of ethyl acetate. After heating at 100° in vacuo overnight 18 had a melting point of 141°-143°: [α]D25 -65.8° (c 1.00, water); nmr (DMSO-d6) δ 5.77 (d, 1, J1',2' 4.0 Hz, 1'--H), 7.34 (s, 1, 5--H).

Provenance & Evidence