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

HRID 581895Notes

Reaction equation

HRID 581895 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H]>C(O)(=O)C.[Pd]>[N:1]1([C:6]2[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=2)[NH2:12])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

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

Product 1

HCID 3212253-(1H-imidazol-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 3-(1-imidazolyl)nitrobenzene (51.6 g, 0.27 mol) in acetic acid (500 ml) is added palladium catalyst (5 g 5% Pd on activated carbon) and the mixture is hydrogenated under pressure (Pstart :4 bar) until the hydrogen uptake has ceased. The mixture is filtered through celite and the filtrate is evaporated to dryness to leave 2d as a light-brown oil. Yield: 40.4 g (93%).

Workup

  1. filtrationThe mixture is filtered through celite
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-ddc97b91405f47cfa0eaba1cdc5c1e0d
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

Loading…