Potassium Carbonate → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

HRID 2392624Notes

Reaction equation

HRID 2392624 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][N:21]([CH2:23][CH2:24]Cl)[CH3:22]>CC(C)=O.O>[CH3:20][N:21]([CH2:23][CH2:24][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 107764242-(2-Dimethylaminoethoxy)-4-nitroanisoleYield 70%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2-methoxy-5-nitrophenol (5.0 g, 0.029 mole) and potassium carbonate (8.3 g, 0.060 mole) in acetone (200 ml) and water (60 ml) was treated with N,N-dimethylaminoethyl chloride hydrochloride (8.64 g, 0.060 mole) and heated under reflux for 10 h. The mixture was concentrated under vacuum to approx. 80 ml volume, then acidified with 2M HCl acid (150 ml) and washed with ethyl acetate (2×80 ml). The acid solution was basified with K2CO3 and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2 SO4) and concentrated under vacuum to afford the title compound as a yellow solid (4.87 g, 70%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 h
  3. concentrationThe mixture was concentrated under vacuum to approx. 80 ml volume
  4. washwashed with ethyl acetate (2×80 ml)
  5. extractionextracted with ethyl acetate (2×100 ml)
  6. extractionThe combined extract
  7. customwas dried (Na2 SO4)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2c941c9d0b0a4995a7d1bb2f125ce5f8
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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