3-(1,2-dimethyl-1H-imidazol-5-yl)nitrobenzene → 3-(1,2-dimethyl-1H-imidazol-5-yl)aniline

HRID 1835482Notes

Reaction equation

HRID 1835482 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=2)=[CH:5][N:4]=[C:3]1[CH3:16]>CO.[Pd]>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:13])=[CH:5][N:4]=[C:3]1[CH3:16]

Participants

4

Reactant 1

HCID 235036903-(1,2-dimethyl-1H-imidazol-5-yl)nitrobenzene

Product 1

HCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)anilineYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-(1,2-dimethyl-1H-imidazol-5-yl)nitrobenzene (19.2 g) in methanol (200 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 5 g) under hydrogen atmosphere for 10 hours. After the catalyst was filtered off, the filtrate was evaporated under reduced pressure. The residue was triturated with ethyl acetate and diisopropyl ether to give 3-(1,2-dimethyl-imidazol-5-yl)aniline (14.65 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was triturated with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-0eb2a3f57efd4257993c6c8aba6074ae
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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