Hydrazine hydrate (1:1) → HCID 178507670, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 39 (28.5 g, 153.87 mmol, 1.00 equiv) in EtOH (300 mL) under N2 was added 85% hydrazine hydrate (5.7 g, 100 mmol, 0.65 equiv), and the reaction mixture was stirred at 80° C. for 6 h. The reaction was cooled to RT, and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with DCM/MeOH gradient (1 to 5% MeOH) to afford 25.4 g (83%) of trans-3-(2-phenylcyclopropyl)-1H-pyrazol-5-amine (41) as a light yellow oil: 1H NMR (400 MHz, DMSO-d6): δ 7.30-7.10 (m, 5H), 5.15 (s, 1H), 4.90-4.20 (br s, 2H), 2.10-2.07 (m, 1H), 2.00-1.95 (m, 1H), 1.35-1.31 (m, 2H), 1H not seen; MS (ESI+) m/z=200 [M+1]+.

Provenance & Evidence