1-[3,3-Dimethylbut-1-en-1-yl]-2-nitrobenzene → 2-(3,3-Dimethylbutyl)aniline

HRID 656803Notes

Reaction equation

HRID 656803 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O.[H][H]>CO.[Pd]>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

5

Reactant 2

HCID 673970311-[3,3-Dimethylbut-1-en-1-yl]-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 236538932-(3,3-Dimethylbutyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1 g (4.87 mmol) of 1-[3,3-dimethylbut-1-en-1-yl]-2-nitrobenzene are stirred in 20 ml of methanol with 0.26 g of palladium/carbon (10%) at 40° C. under 60 bar of hydrogen pressure for 24 hours. Subsequently, the solution is filtered with suction through Celite and the filtrate is concentrated by rotary evaporation. This gives 0.8 g (58% of theory) of an oil. Purity (GC-MS): 63%.

Workup

  1. filtrationSubsequently, the solution is filtered with suction through Celite
  2. concentrationthe filtrate is concentrated by rotary evaporation

Sources & evidence

ORD record
ord-629b2406ba114cd291b01a92b6e638a3
Source dataset
uspto-grants-2011_12
Patent number
US08071824B2

Reaction notes

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