2-Methyl-4-nitrophenol → Dimethyl{2-[(2-methyl-4-nitrophenyl)oxy]ethyl}amine

HRID 1630368Notes

Reaction equation

HRID 1630368 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:12][N:13]([CH2:14][CH2:15][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1])[CH3:17]

Participants

5

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium Carbonate

Product 1

HCID 58377223Dimethyl{2-[(2-methyl-4-nitrophenyl)oxy]ethyl}amineYield 20.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (30 mL) solution of 2 g of 2-methyl-4-nitrophenol, 1.87 g of 2-dimethylaminoethyl chloride and 5.4 g of potassium carbonate was stirred at 120° C. for 23 hours. The reaction liquid was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the crude product was purified through silica gel column chromatography (chloroform/methanol) to obtain 600 mg of the entitled compound as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe crude product was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-828c8110131741a5980858250339e1c0
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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