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

HRID 2044858Notes

Reaction equation

HRID 2044858 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-49a129d6488f4ff8935bb5e90f42a6d7
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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