Sodium Sulfate → 3-Nitro-7-(2-trifluoromethylbenzyloxy)quinoline

HRID 1938335Notes

Reaction equation

HRID 1938335 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)([O-:3])=[O:2].[H-].[Na+].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[C:18]([F:17])([F:27])[F:28])[CH:8]=2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 1357342933-Nitroquinolin-7-ol

Product 1

HCID 214693273-Nitro-7-(2-trifluoromethylbenzyloxy)quinolineYield 53.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In dimethylformamide (DMF, 9 mL) was dissolved 3-nitro-7-hydroxyquinoline (800 mg, 4.24 mmol.). To the solution were added subsequently sodium hydride (168 mg, 4.24 mmol.) and 2-trifluoromethylbenzyl chloride (816 mg, 4.24 mmol.) under chilling with ice. The resulting mixture was stirred overnight at room temperature. After the completion of reaction was confirmed, ethyl acetate and aqueous sodium sulfate were added. The ethyl acetate portion was recovered, washed with water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 790 mg of the desired compound as a white crystalline product, yield 53%.

Workup

  1. temperatureunder chilling with ice
  2. customAfter the completion of reaction
  3. customThe ethyl acetate portion was recovered
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-12e1ad34d6444694aaa9b32168a3deb0
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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