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

HRID 1294472Notes

Reaction equation

HRID 1294472 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]>CN(C=O)C.[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-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

4-tert-Butyl-2-nitrotoluene (200 mg, 1.1 mmol) was dissolved in DMF (10 mL). The catalyst (10% Pd/C, 5 mg) was added and the system was purged with argon then exposed to H2 (1 atm) for 12 h. The mixture was filtered over a pad of diatomaceous earth and the filtrate was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine and dried (MgSO4). Removal of the volatiles in vacuo provided the product 5-tert-butyl-2-methylaniline.

Workup

  1. customthe system was purged with argon
  2. filtrationThe mixture was filtered over a pad of diatomaceous earth
  3. additionthe filtrate was diluted with water
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-e52beee28f4a4e478303d3bb8e55e724
Source dataset
uspto-grants-2007_07
Patent number
US07241758B2

Reaction notes

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