1-(3-nitrophenyl)-1H-imidazole → 3-(1H-imidazol-1-yl)aniline

HRID 2086074Notes

Reaction equation

HRID 2086074 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[N:10]1([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

5

Reactant 2

HCID 8179761-(3-nitrophenyl)-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 3212253-(1H-imidazol-1-yl)anilineYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-(3-nitrophenyl)-1H-imidazole (6.5 g, 34 mmol) in glacial acetic acid (50 ml) was treated with 10% palladium on charcoal (320 mg) and hydrogenated at 50 psi until hydrogen uptake ceased (ca. 3 hours). The mixture was filtered through a glass microfibre filter paper (Whatman GF/A) and evaporated to dryness. The residue was azeotroped twice with toluene to give 3-(imidazol-1-yl)phenylamine as a yellow oil (5.5 g, 100%) which was used without purification. m/z (ES+) 360 (M++H).

Workup

  1. custom(ca. 3 hours)
  2. filtrationThe mixture was filtered through a glass microfibre
  3. filtrationfilter paper (Whatman GF/A)
  4. customevaporated to dryness
  5. customThe residue was azeotroped twice with toluene

Sources & evidence

ORD record
ord-9906bdc6e3c74029a312e2fd527112af
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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