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

HRID 1419821Notes

Reaction equation

HRID 1419821 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]([CH3:25])[CH2:22][CH2:23]Cl>COCCOC>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

HCID 107764242-(2-Dimethylaminoethoxy)-4-nitroanisoleYield 86.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 2-methoxy-5-nitrophenol (10 g, 0.059 mole) in 1,2-dimethoxyethane (80 ml) was treated with saturated aqueous potassium carbonate solution (32 ml) followed by 2-dimethylaminoethyl chloride hydrochloride (8.2 g, 0.057 mole) and heated under reflux for 17 hours. A further quantity of 2-dimethylaminoethyl chloride hydrochloride (4.0 g, 0.029 mole) was added and reflux was continued for 18 hours. The mixture was then concentrated in vacuo and the residue treated with 10% Na2CO3 solution (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (11.8 g, 83%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. temperaturereflux
  4. concentrationThe mixture was then concentrated in vacuo
  5. additionthe residue treated with 10% Na2CO3 solution (100 ml)
  6. extractionextracted with ethyl acetate (2×100 ml)
  7. extractionThe combined extract
  8. dry with materialwas dried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2b53d39b52b496dba516ba2bae9a5d8
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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