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

HRID 1677328Notes

Reaction equation

HRID 1677328 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-hydroxy-4-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-fc5d346c88434e87bd10f8373e181917
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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