4,5-Dimethyl-1-(3-nitrophenyl)imidazole → 3-(4,5-Dimethylimidazol-1-yl)phenylamine

HRID 1835472Notes

Reaction equation

HRID 1835472 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[C:6]=1[CH3:7]>CO.O1CCCC1.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[NH2:14])[C:6]=1[CH3:7]

Participants

5

Reactant 1

HCID 235036474,5-Dimethyl-1-(3-nitrophenyl)imidazole

Product 1

HCID 235036513-(4,5-Dimethylimidazol-1-yl)phenylamineYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4,5-dimethyl-1-(3-nitrophenyl)imidazole (130 mg) in methanol (2 ml) and tetrahydrofuran (2 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 50 mg) under hydrogen atmosphere for 3 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 3-(4,5-dimethyl-imidazol-1-yl)aniline (110 mg, 98.2%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f65dc3ec01844d5995822c079af0df53
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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