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

HRID 443776

Reaction equation

HRID 443776 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1>[Pt].OC1C=C(C=C(O)C=1)C(O)=O.C(C(CC)=O)C>[CH3:4][CH2:3][CH:2]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1)[CH2:7][CH3:6]

Participants

5

Reactant 1

HCID 72483,4-Dimethylaniline

Product 1

HCID 91984N-(1-ethylpropyl)-3,4-dimethylanilineYield 150.2%

Reagents, catalysts & solvents 3

HCID 74243,5-Dihydroxybenzoic AcidCatalystHCID 23939PlatinumCatalystHCID 7288Ethyl ketoneSolvent

Conditions

Temperature
70 °C

Procedure

A Parr hydrogenation apparatus was charged with 1.2 grams 5% platinum on carbon, 0.62 g 3,5-dihydroxybenzoic acid (pKa=1.92), 24.2 grams 3,4-xylidine and 28.0 grams diethyl ketone. The mixture heated to 70° C. and hydrogenated at 35-60 psig. The mixture was cooled, filtered, the filter cake washed with methanol, and the organic phase (87.7 g) analyzed by gas-liquid chromatography. Thus, 28.7 g of N-3-pentyl-3,4-xylidine was obtained, corresponding to a yield of 75.1%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe filter cake washed with methanol

Sources & evidence

ORD record
ord-ff2a6f894ec84657a1b7d52515fa9b8a
Source dataset
uspto-grants-1981_04
Patent number
US04261926

Linked notes

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