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

HRID 38412Notes

Reaction equation

HRID 38412 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-9e4b8690ae714cea8a36d70af5f9d9c2
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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