Water → 8-[2,6-Dichloro-3-(methoxymethoxy)benzyloxy]-2-methylquinoline

HRID 1604561Notes

Reaction equation

HRID 1604561 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[H-].[Na+].[Cl:15][C:16]1[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[C:18]([Cl:26])[C:17]=1[CH2:27]OS(C)(=O)=O.O>CN(C)C=O>[Cl:15][C:16]1[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[C:18]([Cl:26])[C:17]=1[CH2:27][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 132242-Methyl-8-hydroxyquinolineHCID 24758Sodium hydrideHCID 196032302,6-Dichloro-1-methylsulfonyloxymethyl-3-(methoxymethoxy)benzene

Product 1

HCID 196033098-[2,6-Dichloro-3-(methoxymethoxy)benzyloxy]-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8-hydroxy-2-methylquinoline (737 mg) in dimethylformamide was dropwise added to a solution of sodium hydride (60% in oil, 185 mg) in dimethylformamide under ice-bath cooling, and the mixture was stirred for 1 hour at the same temperature. To the mixture was added 2,6-dichloro-1-methylsulfonyloxymethyl-3-(methoxymethoxy)benzene (1.46 g) under ice-bath cooling, and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to give 8-[2,6-dichloro-3-(methoxymethoxy)-benzyloxy]-2-methylquinoline as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 1 hour at the same temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-cfa6cab194ea48ba92f5f2133bb9b483
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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