3,4-Dimethylaniline → N-(1-ethylpropyl)-3,4-dimethylaniline

HRID 443777

Reaction equation

HRID 443777 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([C:12]([CH2:14][CH3:15])=O)[CH3:11]>[Pt].C(O)(=O)C>[CH3:11][CH2:10][CH:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1)[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 72483,4-DimethylanilineHCID 7288Ethyl ketone

Product 1

HCID 91984N-(1-ethylpropyl)-3,4-dimethylanilineYield 72.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Amounts of 24.2 g (0.20 mole) of 3,4-xylidine 38.4 g (0.44 mole) of diethyl ketone, 1.2 g of 5% platinum on carbon, and 0.26 g (2 mole %) of glacial acetic acid were charged to an autoclave and the autoclave was sealed, evacuated, purged with hydrogen and then pressurized with hydrogen to 50 psi. The temperature of the autoclave was raised to 60° C. and held at 60°-68° C. for 0.9 hours (very little, if any, hydrogen was being absorbed at this point). The autoclave was vented and the product filtered to separate the catalyst. The lower, aqueous phase, of the filtrate was separated and the upper, organic phase, was evaporated to constant weight of 35.0 g. Analysis of the residue showed it to be 78.8% pure, corresponding to 28.7 g of N-3-pentyl-3,4-xylidine (72.2% yield).

Workup

  1. customthe autoclave was sealed
  2. customevacuated
  3. custompurged with hydrogen
  4. custom(very little, if any, hydrogen was being absorbed at this point)
  5. filtrationthe product filtered
  6. customto separate the catalyst
  7. customThe lower, aqueous phase, of the filtrate was separated
  8. customthe upper, organic phase, was evaporated to constant weight of 35.0 g

Sources & evidence

ORD record
ord-51a3a87a9dbf4db8800e4981c1101536
Source dataset
uspto-grants-1981_04
Patent number
US04261926

Linked notes

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