Methyl iodide → 4-Methyl-6-nitro-2H-1,4-benzoxazin-3-one

HRID 386660Notes

Reaction equation

HRID 386660 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=1)([O-:5])=[O:4].[CH3:17]I>CN(C=O)C>[CH3:17][N:11]1[C:10]2[CH:16]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=2[O:14][CH2:13][C:12]1=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 14777644-Methyl-6-nitro-2H-1,4-benzoxazin-3-oneYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (0.57 g, 23.75 mmol) was added to a solution of 6-nitro-4H-benzo[1,4]oxazin-3-one (2.3 g, 11.85 mmol) in DMF (50 ml) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then CH3I (1.5 ml, 24.04 mmol) was added. The mixture was stirred at 0° C. for one hour, then at room temperature for one hour. The mixture was partitioned between EtOAc and water. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to give 2.5 g of 4-methyl-6-nitro-4H-benzo[1,4]oxazin-3-one as a solid, 100%.

Workup

  1. stirringThe mixture was stirred at 0° C. for one hour
  2. waitat room temperature for one hour
  3. customThe mixture was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3f0fe7102104d3eb439713aed675545
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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