8-Hydroxyquinoline → HCID 10925920, compound

HRID 1449688Notes

Reaction equation

HRID 1449688 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.[CH3:12][C:13](C)([O-:15])[CH3:14].[K+].Cl[CH2:19][C:20]([CH2:22]Cl)=[CH2:21].[I-].[K+]>O.CN(C)C=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:19][C:20]([CH2:22][O:15][C:13]2[CH:14]=[CH:7][CH:6]=[C:5]3[C:12]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[CH2:21])[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 4875Potassium IodideHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 10925920HCID 10925920, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into 50 ml of dimethylformamide were dissolved 7.0 g (0.048 mol) of 8-quinolinol, to which 5.0 g (0.045 mol) of potassium tert-butoxide were added. The resulting mixture was stirred until a gas ceased generating and the liquid became transparent and thereafter mixed with 2.5 g (0.020 mol) of 2-chloromethyl-3-chloro-1-propene and a small amount of potassium iodide. The mixture was reacted at 70° C. for 24 hours with stirring. The reaction mixture was then cooled to room temperature, mixed with 150 ml of water and extracted thrice with 50 ml of benzene. The benzene phase was washed thrice with 100 ml of water and dried over anhydrous magnesium sulfate. The benzene was removed in vacuo and the residue was subjected to silica gel chromatography using chloroform as an elution liquid, thereby to separate 1.6 g (yield: 47%) of 2-(8-quinolyloxy)methyl-3-(8-quinolyloxy)-1-propene as a colorless solid having a melting point of about 101°-102° C. The chemical structure of this intermediate product was elucidated by NMR, IR and MS. The mass spectrometric analysis gave a molecular weight of 342.1375 (calculated: 342.1367 as C22H18N2O2).

Workup

  1. customThe mixture was reacted at 70° C. for 24 hours
  2. stirringwith stirring
  3. extractionextracted thrice with 50 ml of benzene
  4. washThe benzene phase was washed thrice with 100 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe benzene was removed in vacuo
  7. washas an elution liquid

Sources & evidence

ORD record
ord-23c7776de09445df83b6c3c60ce82da8
Source dataset
uspto-grants-1997_02
Patent number
US05599935

Reaction notes

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