Phenol → HCID 19592390, compound

HRID 613487Notes

Reaction equation

HRID 613487 reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:13][C:14](=[O:23])[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[C:14]([NH:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([CH2:2][O:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:12]2)=[O:23]

Participants

6

Reactant 4

HCID 996PhenolHCID 25517Ammonium ChlorideHCID 195923883-Bromomethyl-8-(2,6-dichlorobenzoylamino)quinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19592390HCID 19592390, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline (120 mg) and phenol (30.3 mg) in dimethylformamide was added potassium tert-butoxide (72.2 mg), and the mixture was stirred for 1 hour at ambient temperature. The mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 8-(2,6-dichlorobenzoylamino)-3-phenoxymethylquinoline (87.1 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-0f61057f436b466ba4b5dc3e66f83154
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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