Nitrogen → 1-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-1H-pyrazol-4-ylamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-4-nitro-1H-pyrazole (1.80 g, 7.05 mmol), iron powder (1.20 g, 21.26 mmol) and NH4Cl (1.90 g, 35.25 mmol) in a mixture of EtOH (46.0 mL) and water (23.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (400 mL) was added followed by 1M NaOH (100 mL). The aq. layer was extracted with CH2Cl2 (2×100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.56 min; [M+H]+=226.53. 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 3H), 1.34-1.46 (m, 2H), 1.61-1.70 (m, 2H), 1.77-1.88 (m, 2H), 2.85 (s, 2H), 3.86-3.92 (m, 2H), 3.92-3.96 (m, 2H), 3.99 (t, J=7.3 Hz, 2H), 7.00 (s, 1H), 7.14 (s, 1H).

Herkunft & Nachweise