Potassium Carbonate → HCID 19968967, compound

HRID 486607Notes

Reaction equation

HRID 486607 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 127627274-(Methoxymethoxy)aniline

Product 1

HCID 19968967HCID 19968967, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8.4 g (54.8 mmol) of 4-methoxymethyloxyaniline and 7.5 g (49 mmol) of 2-chloro-3-nitropyridine were dissolved in 35 ml of dimethylformamide. 7.6 g (55 mmol) of anhydrous potassium carbonate was added to the solution. The resulting solution was heated under stirring at 100° C. for 4 h. The reaction liquid was cooled to room temperature and an insoluble matter thus formed was removed by filtration. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed with an aqueous citric acid solution and then with water. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was recrystallized from ethanol to obtain 9.68 g of the title compound.

Workup

  1. temperatureThe resulting solution was heated
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. customan insoluble matter thus formed
  5. customwas removed by filtration
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe solution was washed with an aqueous citric acid solution
  9. dry with materialAfter drying over magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1955c200516041b2b1882d2cadab4e39
Source dataset
uspto-grants-1994_03
Patent number
US05292758

Reaction notes

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