1-(3-Methylbutoxy)-4-nitrobenzene → Aniline, p-(isopentyloxy)-

HRID 2223786Notes

Reaction equation

HRID 2223786 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 127211661-(3-Methylbutoxy)-4-nitrobenzene2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 21262Aniline, p-(isopentyloxy)-Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Palladium on charcoal (100 mg) was added in one portion to a stirred solution of 1-[(3-methylbutyl)oxy]4-nitrobenzene (intermediate 4, 2.00 g, 9.56 mmol) in ethyl acetate (40 mL) at room temperature under a nitrogen atmosphere. The nitrogen was replaced with hydrogen and stirring was continued for 4 h. The hydrogen was replaced with nitrogen then the crude reaction mixture was filtered through a plug of celite. The solute was evaporated to dryness to give the title compound as a colourless oil (1.71 g, 100%) which was used without purification. LC/MS: 2.29 min; z/e 180, calcd (M+1) 180. 1H NMR (400 MHz; CDCl3): 0.95 (6H), 1.65 (2H), 1.85 (1H), 3.10 (2H), 3.90 (2H), 6.65 (2H), 6.75 (2H).

Workup

  1. customthe crude reaction mixture
  2. filtrationwas filtered through a plug of celite
  3. customThe solute was evaporated to dryness

Sources & evidence

ORD record
ord-29de3c4190b64017ab07c55e39d3daa3
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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