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

HRID 81827Notes

Reaction equation

HRID 81827 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-29538736b1e14b31a50316458b9e72c4
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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