1-tert-Butyl-4-nitrobenzene → 4-Tert-Butylaniline

HRID 329782Notes

Reaction equation

HRID 329782 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[H][H]>[Pd].C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 767731-tert-Butyl-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 698614-Tert-Butylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Absolute ethanol (20 ml) was added to 10% palladium on charcoal (0.2 g) in a Parr hydrogenation bottle (500 ml volume). 1-(1,1-Dimethylethyl)-4-nitrobenzene (50 g) in absolute ethanol (100 ml) was added. Hydrogen was admitted to the bottle and the mixture shaken at 60 psi over night. The catalyst was removed by filtration through Celite under nitrogen, the filtrate was reduced in vacuo and the residue distilled at 96° C./0.3 mm Hg to give 4-(1,1-dimethylethyl)benzenamine as an oil.

Workup

  1. customThe catalyst was removed by filtration through Celite under nitrogen
  2. distillationthe residue distilled at 96° C./0.3 mm Hg

Sources & evidence

ORD record
ord-da660ec63eb844cc9dae326b82405d5f
Source dataset
uspto-grants-1990_01
Patent number
US04892963

Reaction notes

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