Methyl iodide → 2-methoxy-3-methylquinoxaline

HRID 868962Notes

Reaction equation

HRID 868962 reaction equation
[CH3:1][C:2]1[C:3](=[O:12])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:13]I>C1(C)C=CC=CC=1.[Ag]=O>[CH3:13][O:12][C:3]1[C:2]([CH3:1])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 263843-Methylquinoxalin-2-ol

Product 1

HCID 3514302-methoxy-3-methylquinoxalineYield 60.6%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-methylquinoxalin-2(1H)-one (3.2 g, 20 mmol), silver oxide (5.56 g, 24 mmol), and methyl iodide (5.68 g, 40 mmol) in toluene (100 mL) was heated to 100° C. for 16 h. After cooling to room temperature, the reaction mixture was filtered, concentrated, and purified by column chromatography to afford the title compound as an orange solid (2.11 g). MS (ESI): m/z 175 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-5392fac8c7c8408ab6ade445b60a1916
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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