Sodium hydride → 4-[2-(4-Chlorophenyl)ethoxy]-8-fluoroquinoline

HRID 487128

Reaction equation

HRID 487128 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.Cl[C:14]1[C:23]2[C:18](=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:14]2[C:23]3[C:18](=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74647p-Chlorophenethylic alcoholHCID 27365874-Chloro-8-fluoroquinoline

Product 1

HCID 190940614-[2-(4-Chlorophenyl)ethoxy]-8-fluoroquinolineYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 1.2 g of sodium hydride in 50 mL of DMF was added 3.9 g of 2-(4-chlorophenyl)ethyl alcohol. The mixture was stirred at room temperature for one hour, then 4.5 g of 4-chloro-8-fluoroquinoline in 10 mL of DMF was added, the the mixture was heated to reflux for two hours. Then the mixture was allowed to cool to room temperature while it was stirred for four hours, after which it was poured into an ice/water mixture. The mixture was filtered, and the filter cake was washed with H2O. Recrystallization from pentane/ethyl acetate gave 0.840 g of the title product. Yield 11.2%. M.P. 139°-140° C.

Workup

  1. temperaturethe the mixture was heated
  2. temperatureto reflux for two hours
  3. temperatureto cool to room temperature while it
  4. stirringwas stirred for four hours
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with H2O
  7. customRecrystallization from pentane/ethyl acetate

Sources & evidence

ORD record
ord-ed3a2226d3f645fca9d90e8efbf0f51b
Source dataset
uspto-grants-1994_03
Patent number
US05294622

Linked notes

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