Water → 7-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one

HRID 38413Notes

Reaction equation

HRID 38413 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[NH:7][C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[N:7]([CH3:16])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 116007707-Methoxy-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 233230137-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-oneYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

7-Methoxy-4H-benzo[1,4]oxazin-3-one (11.61 g, 0.065 mol) in 100 mL dry DMF was stirred at 0° C. under nitrogen. Sodium hydride (60%, 2.85 g, 0.072 mol) was added in portions over 30 minutes, after which methyl iodide (4.44 mL, 0.071 mol) was added dropwise. The reaction mixture was stirred at 0° C. for 2.5 hours, then poured into 1400 mL water. The resulting aqueous mixture was extracted four times with 400 mL EtOAc, and the combined organic layers were washed with water, then brine, dried (MgSO4), filtered, and evaporated under reduced pressure to provide 13.07 g of 7-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one. (M+H)=194.

Workup

  1. extractionThe resulting aqueous mixture was extracted four times with 400 mL EtOAc
  2. washthe combined organic layers were washed with water
  3. dry with materialbrine, dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8044f7af9b804aae8ef77017c1c02da7
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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