2,4-Dimethyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole → 4-(2,4-Dimethyl-1H-imidazol-1-yl)-2-methylaniline

HRID 568389Notes

Reaction equation

HRID 568389 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]2[CH3:17])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C.[H][H]>C(O)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]2[CH3:17])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 144502562,4-Dimethyl-1-(3-methyl-4-nitrophenyl)-1H-imidazoleHCID 178477803HCID 178477803, compound

Product 1

HCID 144502694-(2,4-Dimethyl-1H-imidazol-1-yl)-2-methylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The following compound was prepared similarly to Preparation 56, using 1-(3-methyl-4-nitrophenyl)-2,4-dimethylimidazole and 5% palladised charcoal/H2 as the starting materials and ethanol as the solvent. The crude solid melted at 78°-82°. Recrystallisation from toluene gave 1-(4-amino-3-methylphenyl)-2,4-dimethylimidazole, m.p. 118°-120° C.

Workup

  1. customThe following compound was prepared similarly to Preparation 56
  2. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-79d65f65b3824a4c8b951f1287be321e
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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