Isopropyl iodide → 4-methoxy-N-(propan-2-yl)aniline

HRID 445149Notes

Reaction equation

HRID 445149 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:10](I)([CH3:12])[CH3:11].C(N(CC)CC)C>CO>[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 7732P-AnisidineHCID 8471Triethylamine

Product 1

HCID 27594984-methoxy-N-(propan-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 g (40.6 mmol) p-anisidin, 4.1 ml (40.6 mmol) isopropyl iodide and 5.7 ml (40.6 mmol) triethylamine in 40 ml methanol is refluxed for 18 h. The reaction mixture is extracted with diethyl ether/water and the organic layers are evaporated. The crude product is purified by flash chromatography using dichloromethane/MeOH (98:2) as eluent to yield isopropyl-(4-methoxy-phenyl)-amine.

Workup

  1. extractionThe reaction mixture is extracted with diethyl ether/water
  2. customthe organic layers are evaporated
  3. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-d5e406d852944d6497d8922df46ec658
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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