Hydrochloric Acid → HCID 10882462, compound

HRID 1732190Notes

Reaction equation

HRID 1732190 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]([Cl:29])[CH:25]=2)[N:20]=1.C1C=CC([O-])=CC=1.[Na+].Cl>CS(C)=O.O>[Cl: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

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1011822-(4-Hydroxy-phenoxy)-propionic acidHCID 141233DisodiumHCID 6075022,6-DichloroquinolineHCID 4445035Phenolate Sodium

Product 1

HCID 10882462HCID 10882462, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

2-(4-Hydroxyphenoxy)propionic acid (2.85 gm, 0.0156 mole) was dissolved in 60 ml of dimethylsulfoxide. A solution of sodium hydroxide (1.25 gm, 0.031 mole) in 2.0 ml of water was added and the mixture stirred for a few minutes to insure complete conversion to the disodium salt. 2,6-Dichloroquinoline (3.1 gm, 0.0126 mole) was dissolved in 50 ml of DMSO and then added all at once to the sodium phenate solution. The reaction mixture was then heated to about 125° C. and stirred at this temperature for 3.0 hours. At the end of this time it was cooled, poured into 350 ml of cold water and acidified with concentrated hydrochloric acid. The precipitated crude product was collected on a filter, washed with fresh water, sucked damp dry and taken up in hot toluene. It was then dried over sodium sulfate, treated with "Norite", filtered and the filtrate concentrated and chilled to precipitate the white crystalline 2-(4-((6-chloro-2-quinolinyl)oxy)phenoxy)propionic acid.

Workup

  1. stirringstirred at this temperature for 3.0 hours
  2. temperatureAt the end of this time it was cooled
  3. customThe precipitated crude product
  4. customwas collected on a filter
  5. washwashed with fresh water
  6. customsucked damp dry
  7. dry with materialIt was then dried over sodium sulfate
  8. additiontreated with "Norite"
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated
  11. temperaturechilled
  12. customto precipitate the white crystalline 2-(4-((6-chloro-2-quinolinyl)oxy)phenoxy)propionic acid

Sources & evidence

ORD record
ord-8685561b1ac145338842b88bfd0f2bdf
Source dataset
uspto-grants-1980_12
Patent number
US04236912

Reaction notes

Loading…