Hydrazine → HCID 136148569, compound

Participants

Reaction Steps

To a solution of 5i (0.100 g, 0.22 mmol) in MeOH (5 mL) and THF (5 mL) was added Raney-Nickel (0.6 mL, 50% slurry in H2O) followed by anhydrous NH2NH2 (0.3 mL, 9.56 mmol). The reaction mixture was stirred 15 min at ambient temperature, filtered using a syringe filter with 0.2 μm PTFE membrane, and concentrated in vacuo. The crude mixture was purified by flash column chromatography using silica gel eluted with 0-3% MeOH/CH2Cl2 to give 5j (0.072 g, 77%) as a red solid. 1H NMR (400 MHz, D6-DMSO) δ 7.0 (br s, 1 H), 6.93 (s, 1 H), 6.79 (d, J=2.8 Hz, 1 H), 6.76 (d, J=2.4 Hz), 5.33 (br s, 2 H), 3.86 (t, J=6.8 Hz, 2 H), 3.22 (m, 1 H), 1.52 (m, 3 H), 1.08 (d, J=7.2 Hz, 6 H), 0.90 (d, J=6.4 Hz, 6 H). MS(ESI+) m/e 420 [M+H]+.

Provenance & Evidence