4,7-Dichloroquinoline → 7-Chloro-4-(4-fluorophenoxy)quinoline

HRID 5544

Reaction equation

HRID 5544 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.N1(C2C=CN=CC=2)CCCC1>C1(C)C(C)=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[C:11]3[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 68664,7-DichloroquinolineHCID 97324-FluorophenolHCID 755674-Pyrrolidinopyridine

Product 1

HCID 1641717-Chloro-4-(4-fluorophenoxy)quinolineYield 649.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a 50 mL flask equipped with a condenser, drying tube and thermometer, was added 1.98 g (0.01 moles) of 4,7-dichloroquinoline, 1.57 g (0.0014 moles) of 4-fluorophenol, 0.22 g (0.0015 moles) of 4-pyrrolidinopyridine and 20 mL of xylene. The reaction mixture was heated to reflux and reaction progress was monitored by TLC. After 18 hr, the mixture was cooled and washed with 50 mL of 5 N NaOH. The caustic layer was extracted with 3×20 mL of diethyl ether. The xylene and the ether layers were combined and dried over Na2SO4. Removal of the solvent provided 2.49 g (91 percent yield) of product, mp=88°-91° C.

Workup

  1. customTo a 50 mL flask equipped with a condenser
  2. customdrying tube
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. customreaction progress
  6. temperaturethe mixture was cooled
  7. washwashed with 50 mL of 5 N NaOH
  8. extractionThe caustic layer was extracted with 3×20 mL of diethyl ether
  9. dry with materialdried over Na2SO4
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-083e912021ea4636b30489d9253b9684
Source dataset
uspto-grants-1993_09
Patent number
US05245036

Linked notes

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