2-Chloroquinoline → 2-(4-(2-Quinolinyloxy)phenoxy)propanoic acid

HRID 1732189Notes

Reaction equation

HRID 1732189 reaction equation
[Na][Na].[OH:3][C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>CS(C)=O.O.C1(C)C=CC=CC=1>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 119282-ChloroquinolineHCID 14798Sodium HydroxideHCID 1011822-(4-Hydroxy-phenoxy)-propionic acidHCID 141233Disodium

Product 1

HCID 137473882-(4-(2-Quinolinyloxy)phenoxy)propanoic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

The disodium salt of 2-(4-hydroxyphenoxy)propionic acid was made by dissolving the acid (9.1 gm, 0.05 mole) in 50 ml of DMSO and adding a solution of sodium hydroxide (4.4 gm, 0.11 mole) in 13 ml of water. The mixture was stirred for 30 min. and warmed to 55° C. at which time a solution of 2-chloroquinoline (8.2 gm, 0.050 mole) in 20 ml of DMSO was added. The reaction mixture was heated at 97°-108° for 1.5 hr. and then at 122°-125° for one hour longer. At the end of this time the mixture was poured into 600 ml of cold water and acidified. It was allowed to stand until solids formed which were taken up in toluene. From this 6.5 gm of 2-(4-(2-quinolinyloxy)phenoxy)propanoic acid were obtained.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated at 97°-108° for 1.5 hr
  3. waitand then at 122°-125° for one hour longer
  4. customformed which

Sources & evidence

ORD record
ord-3c0770f381d14498b14a543e608466ca
Source dataset
uspto-grants-1980_12
Patent number
US04236912

Reaction notes

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