Water → 4-methyl-8-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 576073Notes

Reaction equation

HRID 576073 reaction equation
[H-].[Na+].[N+:3]([C:6]1[C:15]2[O:14][CH2:13][C:12](=[O:16])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:17]I.O>CN(C)C=O>[CH3:17][N:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[C:15]=2[O:14][CH2:13][C:12]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 389971848-Nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 389971764-methyl-8-nitro-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%) (300 mg, 7.50 mmol) was added to a solution of 8-nitro-2 H-1,4-benzoxazin-3(4 H)-one (971 mg, 5.00 mmol) in N,N-dimethylformamide (15 mL) at room temperature, the mixture was stirred for 10 min, and then methyl iodide (374 μL, 6.00 mmol) was added dropwise thereto. The mixture was stirred at room temperature for 3 hr and water was added to the reaction mixture. The resulting precipitate was collected by filtration, washed with ethyl acetate and water, and then dried at 60° C. under reduced pressure to afford 4-methyl-8-nitro-2 H-1,4-benzoxazin-3(4 H)-one as a pale yellow amorphous substance (453 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hr
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with ethyl acetate and water
  4. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-186321116b2e44dc91fadf96bd7afeb6
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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