HCID 10543259, compound → 4-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole

Reaction equation

[C:1]([N:4]([CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[N+:19]([O-])=O)(=O)[CH3:2]>C(O)(=O)C.C(O)C.[Fe]>[CH2:12]([O:11][C:7]1[C:6]2[N:19]=[C:1]([CH3:2])[N:4]([CH2:22][CH3:23])[C:5]=2[CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Procedure

To a solution of N-acetyl-3-benzyloxy-N-ethyl-2-nitroaniline (1.37 g) in acetic acid (11 ml) and ethanol (2.7 ml) was added iron (2.43 g), and the mixture was refluxed for 4 hours. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue was added saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel flash chromatography (hexane—ethyl acetate) to give 4-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole (397 mg).