Potassium Carbonate → 8-Nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

HRID 576072Notes

Reaction equation

HRID 576072 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=1[OH:21])=[O:10]>CN(C)C=O.C(OCC)(=O)C>[N+:18]([C:14]1[C:13]2[O:21][CH2:8][C:9](=[O:10])[NH:11][C:12]=2[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 136462502-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide

Product 1

HCID 389971848-Nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (4.10 g, 29.7 mmol) was added to a solution of 2-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide obtained (5.70 g, 24.7 mmol) in N,N-dimethylformamide (150 mL) while cooling in ice, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was powdered with chloroform and collected by filtration to afford 8-nitro-2 H-1,4-benzoxazin-3(4 H)-one as a pale orange powder (4.32 g).

Workup

  1. temperaturewhile cooling in ice
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8a1bb5b27220403b85e7bccd8087180a
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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