1-Methyl-2-imidazolecarboxaldehyde

• Schiff bases
• ligand N,N-dimethyl-N′-(1-methylimidazole-2-ylmethyl)-ethylenediamine
• [(bis(1-methylimidazol-2-yl)methyl)(2-(pyridyl-2-yl)ethyl)amine]

616-47-7

68-12-2

13750-81-7

A THF solution of n-butyllithium (nBuLi) was added slowly and dropwise to an anhydrous THF (100 mL) solution of 1-methylimidazole (8.2 g, 100 mmol) cooled to -70 °C. The reaction temperature was maintained at -70 °C and after stirring for 30 min, freshly distilled N,N-dimethylformamide (DMF, 7.3 g, 100 mmol) was added. The reaction mixture was continued to be stirred at 0 °C for 2 h. The reaction was subsequently quenched with ice water. The mixture was extracted with ethyl acetate (EtOAc), the organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4). After evaporation of the solvent under reduced pressure, an oily residue was obtained, which was further purified by distillation under reduced pressure to afford the target product 1-methyl-1H-imidazole-2-carbaldehyde in 68% yield. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 9.76 (s, 1H, CHO), 7.22 (s, 1H, Im-CH), 7.07 (s, 1H, Im-CH), 3.96 (s, 3H, CH3). High-resolution mass spectrometry (EI-HRMS) analysis results: m/z calculated value C5H6N2O 110.0480, measured value 110.0481 (100%), 82.0493 (60%).