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

HRID 633468Notes

Reaction equation

HRID 633468 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.[H-].[Na+].[CH3:19]I>C1COCC1>[CH3:1][C:2]1([CH3:16])[C:7](=[O:8])[N:6]([CH3:19])[C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 136655432,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,2-dimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (300 mg, 1.35 mmol, 1 equiv) in 5 mL of THF was added dropwise to mixture of NaH (81 mg, 2.03 mmol, 1.5 equiv., 60%) in 3 mL of THF at 0° C. The mixture was stirred at this temperature for 10 min. Then MeI (0.25 mL, 4.05 mmol, 3 equiv.) was added and the reaction was left at room temperature overnight. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated and concentrated. The residue was purified by column chromatography using a mixture of EtOAC/hexane (1:4) as eluent to give 290 mg (Yield=91%) of product as a pale yellow solid.

Workup

  1. waitthe reaction was left at room temperature overnight
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. additiona mixture of EtOAC/hexane (1:4) as eluent

Sources & evidence

ORD record
ord-ce0e9e3e005640ecad567da4ef67fe3b
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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