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

HRID 966022Notes

Reaction equation

HRID 966022 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-75de4c7c75e54c6d9d9fce5b5a705ca9
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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