Potassium Carbonate → 7-Methoxy-2H-1,4-benzoxazin-3(4H)-one

HRID 2266156Notes

Reaction equation

HRID 2266156 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[OH:14])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][O:14][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 135065532-Chloroacetamido-5-methoxy phenol

Product 1

HCID 116007707-Methoxy-2H-1,4-benzoxazin-3(4H)-oneYield 101%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-N-(2-hydroxy4-methoxy-phenyl)-acetamide (390.0 g, 0.18 mol) and powdered potassium carbonate (27.6 g, 0.2 mol) were added to 1000 mL acetone, and the reaction mixture was refluxed under nitrogen for eight hours. The reaction mixture was cooled, solids were removed by filtration, and the liquid was concentrated under reduced pressure to give 32.56 g of crude 7-Methoxy-4H-benzo[1,4]oxazin-3-one. (M+H)=180.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for eight hours
  2. temperatureThe reaction mixture was cooled
  3. customsolids were removed by filtration
  4. concentrationthe liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aa9b214ab8f040b9b76af57da3d8631a
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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