p-Fluoronitrobenzene → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

To a solution of 1-fluoro-4-nitrobenzene (1.7 g, 12 mmol) in DMF (100 mL) was added 4-methyl-1H-imidazole (0.82 g, 10 mmol) and K2CO3 (11 g, 80 mmol). The mixture was heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and washed with brine (100 mL×2). The organic layer was dried and concentrated. The solid was dissolved in MeOH and bubbled with Ar for 2 min. before adding 10% Pd—C. The hydrogenation was finished in 4 h. The catalyst was removed by filtration and solvent was removed in vacuo to afford title compound (1.5 g, 87%) as brown solid.

1. temperatureThe mixture was heated
2. temperatureat reflux under the argon atmosphere for 20 h
3. filtrationThe mixture was filtered
4. concentrationthe filtrate concentrated in vacuo
5. dissolutionThe residue was dissolved in EtOAc (100 mL)
6. washwashed with brine (100 mL×2)
7. customThe organic layer was dried
8. concentrationconcentrated
9. dissolutionThe solid was dissolved in MeOH
10. custombubbled with Ar for 2 min.
11. additionbefore adding 10% Pd—C
12. customThe catalyst was removed by filtration and solvent
13. customwas removed in vacuo

ORD record

ord-39309d35d80642daabcba139fd8f64ea

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528143B2