Water → 3-Bromo-1-methyl-1,2-dihydroquinolin-2-one

HRID 579371Notes

Reaction equation

HRID 579371 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CI.[C:15](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:12])[N:4]([CH3:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178517115HCID 178517115, compound

Product 1

HCID 2683153-Bromo-1-methyl-1,2-dihydroquinolin-2-oneYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-2-hydroxyquinoline (50 mg, 0.223 mmol) in DMF (1 mL) was added methyl iodide (0.017 mL, 0.268 mmol) and potassium carbonate (46.3 mg, 0.335 mmol.) at room temperature. The reaction mixture was stirred for 16 hours at room temperature. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with water then aqueous saturated sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=/1) to give 3-bromo-1-methylquinolin-2(1H)-one (52 mg, MS: 238.1 [M+H+].)

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=/1)

Sources & evidence

ORD record
ord-4fe1d142d4924fd0becc8e46c51c5a81
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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