Potassium Carbonate → HCID 13386218, compound

HRID 647416Notes

Reaction equation

HRID 647416 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([Cl:26])[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:26][C:18]1[N:17]=[C:16]([O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[C:25]2[C:20]([CH:19]=1)=[CH:21][CH:22]=[CH:23][CH:24]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2986251,3-DichloroisoquinolineHCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetate

Product 1

HCID 13386218HCID 13386218, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-hydroxyphenoxyacetate (1.0 g), 1,3-dichloroisoquinoline (1.0 g), anhydrous potassium carbonate (0.7 g) and dry dimethylformamide (10 ml) was heated, with stirring, at a temperature of 120°-130° C. for a period of 3 hours. The solvent was removed by distillation under reduced pressure and the residue was treated with water. The aqueous mixture was extracted with a mixture of acetone and chloroform and the solvents were removed from the organic extract by distillation under reduced pressure. The residue was chromatographed over silica gel with chloroform elution to give ethyl 4-(3-chloro-1-isoquinolyloxy)phenoxyacetate (1.2 g), mp 97° C. The assigned structure was confirmed by proton magnetic resonance spectroscopy, mass spectrometry and elemental analysis.

Workup

  1. temperaturewas heated
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionthe residue was treated with water
  4. extractionThe aqueous mixture was extracted with a mixture of acetone and chloroform
  5. customthe solvents were removed from the
  6. extractionorganic extract by distillation under reduced pressure
  7. customThe residue was chromatographed over silica gel with chloroform elution

Sources & evidence

ORD record
ord-22efebdb39854178a8726464c9d1be23
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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