Hydrazine hydrate (1:1) → HCID 67492751, compound

Participants

Reaction Steps

A solution of compound 3-methyl-1-(1-methylpiperidin-4-yl)-5-nitroindolin-2-one (0.1 g, 0.345 mmol) in dry methanol (3 mL) was treated with Ra—Ni (0.05 g of wet slurry) followed by hydrazine hydrate (0.1 mL, 3.456 mmol) at room temperature. The resulting mixture was refluxed for 2 min. in a pre-heated oil bath and brought to room temperature. The reaction was filtered through celite bed and washed with methanol (3×10 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 5-amino-3-methyl-1-(1-methylpiperidin-4-yl)indolin-2-one (0.085 g, 96%) as a syrup. 1H NMR (DMSO-d6) δ: 1.24 (d, 3H, J=7.8 Hz), 1.42-1.54 (m, 2H), 1.96 (t, 2H, J=10.2 Hz), 2.18 (s, 3H), 2.26-2.34 (m, 2H), 2.85 (d, 2H, J=11.1 Hz), 3.25-3.30 (m, 1H), 3.91-4.02 (m, 1H), 4.75 (s, 2H), 6.43 (dd, 1H, J=2.1, 8.4 Hz), 6.56 (d, 1H, J=1.5 Hz), 6.79 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %) 260 (MH+, 100).

Provenance & Evidence