4-Chlorophenol → 1-(4-Chlorophenoxy)-3-methyl-4-isoquinoline Acetic Acid

HRID 894393Notes

Reaction equation

HRID 894393 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[C:4]([CH3:16])[N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[C:4]([CH3:16])[N:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 127155131-Chloro-3-methyl-4-isoquinoline acetic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 127155141-(4-Chlorophenoxy)-3-methyl-4-isoquinoline Acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-3-methyl-4-isoquinoline acetic acid (237 mg., 1.01 mmol) prepared as in Example 8, 4-chlorophenol (260 mg., 2.02 mmol), and potassium tert-butoxide (226 mg., 2.02 mmol) were heated at 100° for 3 hr. After cooling the mixture was diluted with ethyl acetate and water and acidified to pH 1-2. The separated aqueous phase was extracted with 20 ml. ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and vacuum evaporated to a brown oil. Chromatography of this on silica gel eluted with ethyl acetate gave a pale yellow solid; 80 mg., 24%, mp 192°-195° d.

Workup

  1. temperaturewere heated at 100° for 3 hr
  2. temperatureAfter cooling the mixture
  3. extractionThe separated aqueous phase was extracted with 20 ml
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customvacuum evaporated to a brown oil
  8. washChromatography of this on silica gel eluted with ethyl acetate
  9. customgave a pale yellow solid

Sources & evidence

ORD record
ord-b080197fdc264089ad06ff7f1185fe00
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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