Sodium Hydroxide → HCID 13747391, compound

HRID 1732188Notes

Reaction equation

HRID 1732188 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[Na][Na].Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=2)[N:20]=1.C1C=CC([O-])=CC=1.[Na+]>CS(C)=O.O>[F:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1)[CH:28]=[CH:27]2

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 1011822-(4-Hydroxy-phenoxy)-propionic acidHCID 141233DisodiumHCID 4445035Phenolate SodiumHCID 150594332-Chloro-6-fluoroquinoline

Product 1

HCID 13747391HCID 13747391, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

2-(4-Hydroxyphenoxy)propionic acid (2.5 gm, 0.0127 mole) was dissolved in 50 ml of DMSO. A solution of sodium hydroxide (1.04 gm, 0.026 mole) in 3.0 ml of water was added and the mixture was stirred for a few minutes to insure complete conversion to the disodium salt. 2-Chloro-6-fluoroquinoline (2.5 gm, 0.0137 mole) was dissolved in 45.0 ml of DMSO and then added all at once to the sodium phenate solution. The reaction mixture was then heated to 125° C. and stirred under nitrogen at this temperature for 1.5 hr. At the end of this time it was cooled and poured into 400 ml of cold water. The aqueous mixture was washed with methylene chloride to remove a small amount of insolubles present and the aqueous layer was separated and acidified to pH 1 with concentrated hydrochloric acid. The phenoxy acid liberated was extracted with methylene chloride. Removal of the solvent left the crude product which was taken up in hot toluene, dried with sodium sulfate and decolorized with "Norite". After removal of about two-thirds of the volume of toluene and addition of hexane, the product, 2-(4-((6-fluoro-2-quinolinyl)oxy)phenoxy)propionic acid, precipitated as a white solid.

Workup

  1. stirringstirred under nitrogen at this temperature for 1.5 hr
  2. temperatureAt the end of this time it was cooled
  3. washThe aqueous mixture was washed with methylene chloride
  4. customto remove a small amount of insolubles present
  5. customthe aqueous layer was separated
  6. extractionThe phenoxy acid liberated was extracted with methylene chloride
  7. customRemoval of the solvent
  8. waitleft the crude product which
  9. dry with materialdried with sodium sulfate
  10. customAfter removal
  11. additionof about two-thirds of the volume of toluene and addition of hexane
  12. customthe product, 2-(4-((6-fluoro-2-quinolinyl)oxy)phenoxy)propionic acid, precipitated as a white solid

Sources & evidence

ORD record
ord-9447d1c6688e4d81b56faf0191465edb
Source dataset
uspto-grants-1980_12
Patent number
US04236912

Reaction notes

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