8-Hydroxyquinoline → Methyl 2-[(quinolin-8-yl)oxy]propanoate

HRID 1029338Notes

Reaction equation

HRID 1029338 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.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23]>CC(=O)CC.O>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[O:1][CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 19899636Methyl 2-[(quinolin-8-yl)oxy]propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

23.2 g of 8-hydroxyquinoline are dissolved in 400 ml of butan-2-one, under the influence of heat, and 30 g of potassium carbonate are added in portions. The mixture is refluxed for one hour. 2 g of potassium iodide are then added dropwise, followed by 40 g of methyl 2-bromopropionate in 100 ml of butan-2-one in the course of one hour, with stirring and boiling. The mixture is then refluxed for another 10 hours. After cooling to room temperature, the mixture is poured onto 1 liter of water and extracted with three 200 ml portions of ethyl acetate. The combined extracts are washed once with 50 ml of water, dried over sodium sulfate and filtered. The solvent is evaporated off and the oily residue is crystallised by trituration with petroleum ether. After recrystallisation from hexane, methyl 2-(8-quinolinoxy)-propionate (compound No.3) is obtained in the form of beige-coloured crystals of melting point 70° to 72° C.

Workup

  1. temperatureof heat
  2. temperatureThe mixture is refluxed for one hour
  3. temperatureThe mixture is then refluxed for another 10 hours
  4. extractionextracted with three 200 ml portions of ethyl acetate
  5. washThe combined extracts are washed once with 50 ml of water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent is evaporated off
  9. customthe oily residue is crystallised by trituration with petroleum ether
  10. customAfter recrystallisation from hexane

Sources & evidence

ORD record
ord-9d799e3684be43caa8fbea6e0bcd8cb5
Source dataset
uspto-grants-1992_04
Patent number
US05102445

Reaction notes

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