2-(Dimethylamino)ethanol → HCID 20238619, compound

HRID 364913Notes

Reaction equation

HRID 364913 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[H][H].[Cl:11][C:12]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>CN(C)C=O>[ClH:11].[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:12]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 132001832-Chloro-3-(4-fluorophenyl)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 20238619HCID 20238619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Dimethylaminoethanol (1.07 g.) was added dropwise to a suspension of sodium hydride (0.56 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (25 ml.) at 0°-5°. When all the hydrogen had evolved, 2-chloro-3-(4-fluorophenyl)quinoline (2.69 g.) was added and the mixture was stirred at ambient temperature for 16 hr. The mixture was then poured into ice-water (500 ml.) and extracted with ethyl acetate (5×100 ml.). The ethyl acetate extract was washed successively with water (50 ml.) and saturated brine (50 ml.), and then dried (MgSO4). The solvent was evaporated under reduced pressure and the residual oil was chromatographed on basic alumina (100 g.; Brockmann Grade III), eluted with increasing concentrations of ethyl acetate in petroleum ether. The eluate obtained with 10% v/v ethyl acetate in petroleum ether was evaporated. The residual oil was dissolved in diethyl ether (100 ml.), and ethereal hydrogen chloride was added until precipitation was complete. The mixture was filtered and the solid residue was crystallised from methanol-ethyl acetate to give 2-(2-dimethylaminoethoxy)-3-(4-fluorophenyl)quinoline hydrochloride, m.p. 168°-171°.

Workup

  1. customat 0°-5°
  2. extractionextracted with ethyl acetate (5×100 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed successively with water (50 ml.) and saturated brine (50 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residual oil was chromatographed on basic alumina (100 g.; Brockmann Grade III)
  8. washeluted
  9. temperaturewith increasing concentrations of ethyl acetate in petroleum ether
  10. customThe eluate obtained with 10% v/v ethyl acetate in petroleum ether
  11. customwas evaporated
  12. dissolutionThe residual oil was dissolved in diethyl ether (100 ml.)
  13. additionethereal hydrogen chloride was added until precipitation
  14. filtrationThe mixture was filtered
  15. customthe solid residue was crystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-79036a493d2d47f597a68923b9c428d0
Source dataset
uspto-grants-1986_08
Patent number
US04607040

Reaction notes

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