4-Tert-butyl-1-methyl-2-nitrobenzene → 5-tert-Butyl-2-methylaniline

HRID 246023Notes

Reaction equation

HRID 246023 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([CH:6]=1)[NH2:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 109544154-Tert-butyl-1-methyl-2-nitrobenzene

Product 1

HCID 130899795-tert-Butyl-2-methylanilineYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-tert-butyl-1-methyl-2-nitrobenzene (3.58 g, 18.5 mmol) in MeOH (80 ml) was added 10% Pd on carbon (wet, 358 mg). The reaction mixture was stirred under an atmosphere of hydrogen (balloon) for 4 h then filtered over Celite, rinsing with EtOAc. The filtrate was concentrated to afford 2.48 g (82%) of 5-tert-butyl-2-methylaniline as a brown oil which was used without further purification.

Workup

  1. filtrationthen filtered over Celite
  2. washrinsing with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2e2cc72e0ee140c4a117bde41e882c50
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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