3-Chloropropionic acid → 3-(5-Quinolinoxy)-propionic acid

HRID 47058

Reaction equation

HRID 47058 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>[OH-].[K+]>[N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([O:1][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 78993-Chloropropionic acidHCID 135441757Quinolin-5-ol

Product 1

HCID 203850343-(5-Quinolinoxy)-propionic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent3×

Procedure

A solution of 5-hydroxyquinoline (4.91 g, 0.0340 mole) (Aldrich) in 17 ml 2 N potassium hydroxide was refluxed while an ice cold solution of 3-chloropropionic acid (4.05 g, 0.0373 mole) (Aldrich) in 18.6 ml 2 N potassium hydroxide was added during 1 minute. The pH was maintained at pH 9.5 by addition of 2 N potassium hydroxide. After 10 minutes, the mixture was allowed to come to room temperature and stirred for 16 hours. The pH of the solution was adjusted to pH 3.8 and the mixture evaporated in vacuo to a residue which was column chromatographed on silica gel by elution with 4:1 ethyl acetate:methanol. Material of Rf =0.45 (thin layer chromatography using 1:1 ethyl acetate:methanol) was obtained and recrystallized from water; m.p. 217°-219° C.

Workup

  1. additionwas added during 1 minute
  2. customto come to room temperature
  3. customthe mixture evaporated in vacuo to a residue which
  4. customchromatographed on silica gel by elution with 4:1 ethyl acetate
  5. customMaterial of Rf =0.45 (thin layer chromatography using 1:1 ethyl acetate:methanol) was obtained
  6. customrecrystallized from water

Sources & evidence

ORD record
ord-66f3661c35384156af4785ba593c9265
Source dataset
uspto-grants-1979_11
Patent number
US04176185

Linked notes

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