Methylhydrazine → 3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine

Participants

Reaction Steps

To an ice-cooled solution of 2-(3-(2,5-Dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione (0.050 g, 0.13 mmol) in ethanol (6 mL) was added 40% aqueous methylhydrazine solution (45 mg, 0.39 mmol). The mixture was then heated at reflux for 3 hours. The reaction mixture was then concentrated and purified by flash column chromatography to afford 3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine as a solid (12 mg, 38% yield). 1H NMR (400 MHz, CDCl3): 7.50 (d, J=3.6 Hz, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.28 (m, 1H), 7.06 (s, 1H), 3.86 (s, 3H), 2.98 (s, 2H).

Provenance & Evidence