Methyl iodide → HCID 58257133, compound

Participants

Reaction Steps

To a solution of 2-(2,5-dimethyl-4-nitrophenyl)-1H-imidazole (50 mg, 0.23 mmol) in DMF (2 mL) was added NaH (11 mg, 0.46 mmol) at 0° C. After stirring for 15 min, iodomethane (65 mg, 0.46 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 hr, and quenched by adding saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate (3×15 mL). The organic layer was washed with brine and dried over sodium sulfate. After concentration, the residue was dissolved in methanol (10 mL). To the solution was added Pd/C (10%). The reaction mixture was degassed and purged with H2 for several times and stirred under 1 atm. hydrogen gas overnight. The mixture was filtered and concentrated to afford 2,5-dimethyl-4-(1-methyl-1H-imidazol-2-yl)aniline. ESMS m/z 202 (M+H+).

Provenance & Evidence