Water → 1,4-Dimethylquinoxaline-2,3-dione

HRID 2094937Notes

Reaction equation

HRID 2094937 reaction equation
[H-].[Na+].N1[C:12]2[C:7](=C[CH:9]=[CH:10][CH:11]=2)[NH:6][C:5](=[O:13])C1=O.[CH3:15]I.O.[CH3:18][N:19]([CH:21]=[O:22])[CH3:20]>>[CH3:18][N:19]1[C:20]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]([CH3:15])[C:5](=[O:13])[C:21]1=[O:22]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 274912,3-Dihydroxyquinoxaline

Product 1

HCID 3514211,4-Dimethylquinoxaline-2,3-dioneYield 95%

Procedure

To a solution of NaH (2.5 g) in DMF (200 mL) was added quinoxaline-2,3(1H,4H)-dione (5 g) in portions, followed by the slow addition of methyl iodide (3.8 mL). The reaction mixture was stirred at ambient temperature for 4 hours, then water was added (200 mL). The resulting precipitate was collected by filtration and washed with water to afford 1,4-dimethylquinoxaline-2,3(1H,4H)-dione as a white solid in 95% yield. 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.50(s, 6H), 7.25(m, 2H), 7.38(m, 4H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-1715a56715cb4abe96746f43c10d9a19
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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