Methyl Ethyl Ketone → N-(1-methylpropyl)-3,4-dimethyl-aniline

HRID 1111881Notes

Reaction equation

HRID 1111881 reaction equation
[CH2:1]([C:3]([CH3:5])=O)[CH3:2].[CH3:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[CH3:14])[NH2:10]>C1C=CC=CC=1>[CH:3]([NH:10][C:9]1[CH:11]=[CH:12][C:13]([CH3:14])=[C:7]([CH3:6])[CH:8]=1)([CH2:1][CH3:2])[CH3:5]

Participants

4

Reactant 2

HCID 6569Methyl Ethyl KetoneHCID 72483,4-Dimethylaniline

Product 1

HCID 13692865N-(1-methylpropyl)-3,4-dimethyl-anilineYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Molecular sieves (Type 5A, 300 gm.) are added to 79.2 g. (1.0 mole) of methyl ethyl ketone and 121.0 g. (1.0 mole) of 3,4-dimethylaniline in 1 liter of dry benzene solvent. The reaction mixture is stirred at room temperature for 16 hours. The mixture is then filtered from the molecular sieves which are washed with dry benzene. The benzene solutions are combined and evaporated in vacuo leaving 198 g. (100%) of the desired product. The product is sensitive to hydrolysis and is therefore reduced immediately in a Parr hydrogenator using a 5% palladium on carbon catalyst to give N-sec-butyl-3,4-xylidine.

Workup

  1. filtrationThe mixture is then filtered from the molecular sieves which
  2. washare washed with dry benzene
  3. customevaporated in vacuo
  4. customleaving 198 g

Sources & evidence

ORD record
ord-af8ed4b02e3c4e57871265d11028fc4f
Source dataset
uspto-grants-1978_10
Patent number
US04119669

Reaction notes

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