Methyl iodide → 7-Bromo-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871968Notes

Reaction equation

HRID 871968 reaction equation
[Br:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:16])([CH3:15])[C:8](=[O:14])[NH:9]2)=[CH:4][CH:3]=1.CI.[C:19](=O)([O-])[O-].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:16])([CH3:15])[C:8](=[O:14])[N:9]2[CH3:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 576720007-Bromo-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576719517-Bromo-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-bromo-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 5, 62.7 mg, 0.220 mmol), methyl iodide (68.6 μL, 1.10 mmol), and cessium carbonate (180 mg, 0.552 mmol) was suspended in anhydrous N,N-dimethylformamide (1 mL) and stirred at room temperature for 2.5 hours. Ethyl acetate (10 mL) and water (10 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (10 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (45.5 mg) as an orange amorphous product. (Yield 69%)

Workup

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a7005852a22341848ba19a21d70a8f9b
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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