反应详情

Ammonium formate (2.202 g, 34.9 mmol) and palladium (10% w/w on carbon, 50% wet, 0.473 g, 4.44 mmol) were added to a solution of 4-methyl-1-(4-nitrophenyl)-1H-imidazole (for a preparation see intermediate 93) (4.73 g, 23.28 mmol) in ethanol (150 mL) and the resulting mixture was refluxed under nitrogen for 1 h then cooled to room temperature. An extra portion of ammonium formate (2.202 g, 34.9 mmol) was then added and the resulting mixture was refluxed for a further hour then cooled to room temperature and filtered through celite. Most of the solvent was removed in vacuo and the residue was loaded on a 50 g SCX column which was eluted with MeOH (5 CV) then with 2N NH3 in MeOH (5 CV). The ammonia fractions were combined and concentrated in vacuo to give 4-(4-methyl-1H-imidazol-1-yl)aniline (3.92 g, 21.06 mmol, 90%) as a yellow solid.

1. temperaturethe resulting mixture was refluxed under nitrogen for 1 h
2. temperaturethe resulting mixture was refluxed for a further hour
3. temperaturethen cooled to room temperature
4. filtrationfiltered through celite
5. customMost of the solvent was removed in vacuo
6. washwas eluted with MeOH (5 CV)
7. concentrationconcentrated in vacuo