Ethyl ketone → N-(1-ethylpropyl)-3,4-dimethylaniline

HRID 443778Notes

Reaction equation

HRID 443778 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([CH3:10])=[CH:8][CH:9]=1)([O-])=O.[CH2:12]([C:14]([CH2:16][CH3:17])=O)[CH3:13].[H][H]>[Pt].O.C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>[CH2:12]([CH:14]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([CH3:11])[CH:5]=1)[CH2:16][CH3:17])[CH3:13]

Participants

6

Reactant 3

HCID 7288Ethyl ketoneHCID 74404-Nitro-o-xyleneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 91984N-(1-ethylpropyl)-3,4-dimethylanilineYield 99.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 20499058Naphthalene-2-sulfonic acid--water (1/1)Catalyst

Procedure

A mixture of 151 grams (1.0 mole) 4-nitro-o-xylene, 138 grams (1.6 moles) diethyl ketone, 5.8 grams of 5% platinum on carbon and 3.7 grams of 2-naphthalenesulfonic acid monohydrate were added to a pressure vessel. Hydrogen was fed into the reactor at a pressure of 30-40 psi and a temperature of 80°-100° C. When hydrogen uptake ceased, the vessel was cooled and vented. After filtering the catalyst, the aqueous phase was separated and the upper layer concentrated in vacuo to give 191 grams of 96% pure N-(1-ethylpropyl)-3,4-xylidine (96% yield).

Workup

  1. additionwere added to a pressure vessel
  2. customa temperature of 80°-100° C
  3. temperaturethe vessel was cooled
  4. filtrationAfter filtering the catalyst
  5. customthe aqueous phase was separated
  6. concentrationthe upper layer concentrated in vacuo

Sources & evidence

ORD record
ord-57096514b3cc4ab5a08feee813577c3d
Source dataset
uspto-grants-1981_04
Patent number
US04261926

Reaction notes

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