4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole → 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

Beteiligte Stoffe

Reaktionsschritte

Step K (2): 10% Palladium on carbon (1.0 g) was added under an atmosphere of nitrogen to a solution of 4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole (10.0 g, 42.9 mmol) in methanol (100 mL). The flask was repeated evacuated and flushed with hydrogen gas. The resulting mixture was allowed to stir at rt for 16 h under. The reaction vessel was purged with nitrogen gas. The crude reaction mixture was filtered through a short diatomaceous earth (Celite®) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline (6.8 g, 78% yield). LC-MS (M+H)+ 204.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.84 (s, 1 H) 7.66 (s, 1 H) 7.19 (d, J=8.2 Hz, 1 H) 6.28 (s, 1 H), 6.18 (d, J=8.2 Hz, 1 H) 5.31 (br s, 1 H), 3.88 (s, 3 H), 3.74 (s, 3 H).

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