Phenol → 8-Chloro-2-phenoxyquinoline-3-carbaldehyde

HRID 216782Notes

Reaction equation

HRID 216782 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([O:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 149171252,8-Dichloro-quinoline-3-carbaldehyde

Product 1

HCID 577078468-Chloro-2-phenoxyquinoline-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,8-dichloroquinoline-3-carbaldehyde (1 eq) in DMF (0.25 M) was added phenol (1.5 eq) and K2CO3 (2.0 eq) at rt and the mixture was stirred for 3 h at rt. The mixture was diluted with water, extracted with EtOAc (2 times) and the combined organic layers were washed with water (2 times), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on a Redi-Sep™ column using 0 to 40% gradient of EtOAc in hexane to provide 8-chloro-2-phenoxyquinoline-3-carbaldehyde.

Workup

  1. extractionextracted with EtOAc (2 times)
  2. washthe combined organic layers were washed with water (2 times)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on a Redi-Sep™ column

Sources & evidence

ORD record
ord-3ee88848756e48899daf8f08406084e1
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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