4,7-Dichloroquinoline → Quinoline, 7-chloro-4-(1-(2-fluorophenyl)ethoxy)-

HRID 487579Notes

Reaction equation

HRID 487579 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9].Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=2)[N:15]=[CH:14][CH:13]=1.[H-].[Na+]>CN(C=O)C.O>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([O:10][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[CH3:9])=[CH:13][CH:14]=[N:15]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 68664,7-DichloroquinolineHCID 24758Sodium hydride2×HCID 1230662-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 164193Quinoline, 7-chloro-4-(1-(2-fluorophenyl)ethoxy)-

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
160 °C

Procedure

A solution of 2.52 g (18 mmol) of 1-(2-fluorophenyl)ethanol in DMF was added dropwise to a mixture of 2.97 g (15mmol) of 4,7-dichloroquinoline and 0.50 g (21 mmol) of sodium hydride in 15 ml of DMF. After addition was complete, the mixture was heated to 160° C. After four hours the mixture was allowed to cool and 0.1 g of sodium hydride was added. Upon completion of the reaction, a few drops of water were carefully added to destroy excess sodium hydride. Then the solution was poured into water. The product was extracted into ethyl acetate, the ethyl acetate solution was washed three times with water, then dried, and evaporated, producing an oil that crystallized from heptane/ethyl acetate. Yield: 0.77 g M.P. 53°-54° C.

Workup

  1. additionAfter addition
  2. temperatureto cool
  3. additionwere carefully added
  4. customto destroy excess sodium hydride
  5. additionThen the solution was poured into water
  6. extractionThe product was extracted into ethyl acetate
  7. washthe ethyl acetate solution was washed three times with water
  8. customdried
  9. customevaporated
  10. customproducing an oil that
  11. customcrystallized from heptane/ethyl acetate

Sources & evidence

ORD record
ord-6f19646f85ac4b8fa0c7faf811555514
Source dataset
uspto-grants-1994_03
Patent number
US05296484

Reaction notes

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