Hydrazine hydrate (1:1) → HCID 56593856, compound

Participants

Reaction Steps

Compound 109 (0.4 g, 1.485 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) and hydrazine hydrate (0.46 mL, 1.029 mmol). The resulting mixture was placed in a pre-heated oil bath and refluxed for 2 min (until yellow colour disappears). The reaction was brought to room temperature, filtered through celite bed and washed with methanol (3×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 110 (0.35 g, quantitative) as a foam. mp 65-67° C.; 1H NMR (DMSO-d6) δ 1.42-1.54 (m, 2H), 1.62-1.74 (m, 2H), 2.52-2.56 (m, 2H), 2.86-2.94 (m, 2H), 2.98-3.02 (m, 1H), 4.75 (s, 2H), 6.41 (dd, 1H, J=2.1, 8.4 Hz), 6.53 (d, 1H, J=1.8 Hz), 6.69 (s, 1H), 7.16 (d, 1H, J=2.4 Hz), 7.35 (d, 1H, J=8.4 Hz), 10.57 (s, 1H); ESI-MS (m/z, %): 240 (MH+, 100).

Provenance & Evidence