(1H-Imidazol-4-yl)methanamine

Synthesis

(1H-imidazol-4-yl)methanamine is prepared by adding hydroxylamine hydrochloride to a reaction mixture of 4-imidazolecarboxaldehyde, sodium carbonate and distilled water.
Experiment steps：Hydroxylamine hydrochloride (1.27 g, 18.3 mmol) was added to a reaction mixture of 4-imidazolecarboxaldehyde (800 mg, 8.3 mmol), sodium carbonate (445 mg, 4.2mmol) and distilled water (14 ml) and was left to react overnight at room temperature with stirring. The resultant mixture was then concentrated in vacuo to 3 ml and placed in an ice bath for precipitation to occur. Solid formed was collected by filtration, dissolved and recrystallized in ethanol to afford the colourless powder oxime, 1H-imidazole-4-carbaldehyde oxime (330 mg). Acetyl chloride (1.06 ml) was added dropwise into methanol (39 ml) in a round bottom flask at 0 °C under nitrogen purge and left to stir for 30 minutes. The oxime was then added into the reaction mixture followed by addition of palladium on carbon, 5% (296 mg, 2.40 mmol). The reaction mixture was hydrogenated at atmospheric pressure overnight. The resultant mixture was then filtered through celite pad, washed with methanol (30 ml) where the filtrate was then collected and concentrated in vacuo to give (1H-imidazol-4-yl)methanamine as a colourless powder (274 mg, 34%).