1-Mesityl-2-methyl-3-nitrobenzene → 3-Mesityl-2-methylaniline

HRID 584814Notes

Reaction equation

HRID 584814 reaction equation
[C:1]1([CH3:19])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[CH3:18]>C(O)C.[H][H].[C].[Pd]>[C:1]1([CH3:19])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[C:10]([CH3:18])=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH2:15]

Participants

5

Reactant 1

HCID 222496861-Mesityl-2-methyl-3-nitrobenzene

Product 1

HCID 222495383-Mesityl-2-methylanilineYield 84.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Palladium-carbon (10%, 1.1 g) was added to a solution of 1-mesityl-2-methyl-3-nitrobenzene (11.0 g, 43 mmol) in ethanol (220 mL) at room temperature, followed by stirring for one day in hydrogen atmosphere. The mixture was filtered through Celite and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (8.2 g) as white crystals.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated
  3. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-256bae7ffcc44057a019d2c71435184f
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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