Hydrazine hydrate (1:1) → 462649-11-2

Participants

Reaction Steps

A suspension of compound 91 (250 mg, 1.07 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (0.33 mL, 10.7 mmol) and the resulting mixture was refluxed for 20 min. The dark green reaction was cooled to room temperature, filtered through a celite pad, washed with methanol (2×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 92(119 mg, 55%) as a yellow oil. 1H NMR (CDCl3) δ 7.16 (d, J=8.7 Hz, 1H), 7.05 (d, J=3.0 Hz, 1H), 6.92 (d, J=2.1 Hz, 1H), 6.67 (dd, J=2.1, 8.7 Hz, 1H), 6.30 (d, J=3.0 Hz, 1H), 4.17 (t, J=7.2 Hz, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.29 (s, 6H); ESI-MS (m/z, %): 204 (M+1).

Provenance & Evidence