Ethanol → HCID 68968504, compound

HRID 540850Notes

Reaction equation

HRID 540850 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:16]2[C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH3:18].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(O)C>CN(C=O)C>[CH3:3][N:4]1[C:16]2[C:15]3[CH:14]=[C:13]([O:17][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 68971275HCID 68971275, compound

Product 1

HCID 68968504HCID 68968504, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.61 g, 15 mmol, available as a 60% dispersion in mineral oil) was added to a solution of 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-ol (2.5 g, 12 mmol) in DMF. The reaction mixture was stirred for 30 minutes, and ethyl bromoacetate (1.96 g, 11.7 mmol) was added. The stirring was continued for five hours, and a small volume of ethanol was added. The volatiles were removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed three times with deionized water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting yellow solid was recrystallized from ethyl acetate to provide 1.65 g of ethyl 2-[(1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]acetate as a white solid.

Workup

  1. waitThe stirring was continued for five hours
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe resulting solution was washed three times with deionized water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting yellow solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c73d4f25679a497bae6ba36f3c2eed18
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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