Water → 2-(3-Methylbutyl)aniline

HRID 1359941Notes

Reaction equation

HRID 1359941 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][CH:10]([CH3:12])[CH3:11].O.NN.[OH-].[K+].O>C(O)COCCOCCO.C(OCC)(=O)C>[CH3:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 122976091-(2-Aminophenyl)-3-methylbutan-1-one

Product 1

HCID 187640942-(3-Methylbutyl)anilineYield 72.1%

Reagents, catalysts & solvents 2

HCID 8172Triethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

A solution comprising 8.0 g (0.045 mol) of 1-(2-aminophenyl)-3-methylbutan-1-one (X-1), 6.8 g (0.135 mol) of hydrazine hydrate and 7.6 g (0.135 mol) of potassium hydroxide in 90 ml of triethylene glycol is heated at 210° C. for 6 h. For work-up, water and ethyl acetate are added at room temperature. The organic phase is again washed with water, dried over magnesium sulphate and concentrated under reduced pressure. Purification by column chromatography (cyclohexane/ethyl acetate 3:1) gives 5.3 g (71.5% of theory) of [2-(3-methylbutyl)-phenyl]amine.

Workup

  1. washThe organic phase is again washed with water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by column chromatography (cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-cb8e894fb6f642e68ae41001b4f15a85
Source dataset
uspto-grants-2011_02
Patent number
US07879760B2

Reaction notes

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