8-Hydroxyquinoline → Propanoic acid, 3-(8-quinolinyloxy)-

HRID 47056

Reaction equation

HRID 47056 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>[OH-].[K+]>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[O:1][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 19238-HydroxyquinolineHCID 78993-Chloropropionic acid

Product 1

HCID 11287391Propanoic acid, 3-(8-quinolinyloxy)-Yield 25%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent3×

Procedure

A solution of 8-hydroxyquinoline (43.5 g, 0.30 mol) (Aldrich) in 150 ml 2 N potassium hydroxide was refluxed while an ice cold solution of 3-chloropropionic acid (36 g, 0.33 mol) (Aldrich) in 165 ml 2 N potassium hydroxide was added over 15 minutes. The pH of the reaction was maintained at pH 10 by addition of 5 N potassium hydroxide during the addition and the subsequent 1.5 hour reflux period. After cooling and filtration the mixture was brought to pH with 6 N hydrochloric acid and extracted with 6×100 ml chloroform. The aqueous layer was acidified to pH 3.8 with 6 N hydrochloric acid and the precipitate thus formed was filtered and washed thoroughly with water, to yield 3-[8-quinolinoxy]-propionic acid (16.12 g, 25% yield), m.p. 211°-213° C.

Workup

  1. additionwas added over 15 minutes
  2. temperaturethe subsequent 1.5 hour reflux period
  3. temperatureAfter cooling
  4. filtrationfiltration the mixture
  5. extractionextracted with 6×100 ml chloroform
  6. customthe precipitate thus formed
  7. filtrationwas filtered
  8. washwashed thoroughly with water

Sources & evidence

ORD record
ord-a9a5b1511fab4420a79bf57a9f19f41a
Source dataset
uspto-grants-1979_11
Patent number
US04176185

Linked notes

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