1-(2-Methyl-1-propenyl)-3-nitrobenzene → 3-Isobutylaniline

HRID 249141Notes

Reaction equation

HRID 249141 reaction equation
[CH3:1][C:2]([CH3:13])=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[CH:5]=1>CO.Cl.[Pd]>[CH2:3]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)[CH:2]([CH3:13])[CH3:1]

Participants

5

Reactant 1

HCID 118161771-(2-Methyl-1-propenyl)-3-nitrobenzene

Product 1

HCID 190247993-IsobutylanilineYield 103.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(2-methyl-1-propenyl)-3-nitrobenzene (4.57 g) in a mixture of methanol (50 ml) and 6N hydrochloric acid (14 ml) was added 10% palladium on activated carbon (1 g), and the mixture was stirred under hydrogen atmosphere (3 atm) at 25° C. for 3 hours. The catalyst was filtered off, and the filtrate was evaporated. The residue was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave 3-isobutylphenylamine (3.98 g) as a brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2564850177c84120a6750dffd2d101d7
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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