HCID 54476165, compound → HCID 66645913, compound

HRID 655647Notes

Reaction equation

HRID 655647 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9](OCC)=[O:10])=[C:5]([N+:18]([O-])=O)[CH:4]=1>[C].[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[O:7][C:8]([CH3:15])([CH3:14])[C:9](=[O:10])[NH:18][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 54476165HCID 54476165, compound

Product 1

HCID 66645913HCID 66645913, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5% palladium carbon (1.5 g) were added to an ethanol solution (250 ml) of ethyl 2-(4-methoxy-2-nitrophenoxy)-2-methylpropionate (14.6 g, 51.6 mmol) to perform catalytic reduction at room temperature. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the obtained residue, which was then extracted with ethyl acetate. The extraction solution was dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1). The purified product was concentrated to dryness under reduced pressure to obtain 6-methoxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.0 g) as white powder.

Workup

  1. customat room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the obtained residue, which
  5. extractionwas then extracted with ethyl acetate
  6. dry with materialThe extraction solution was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)
  9. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2913df16b10841aaa446cb4978ef6e3a
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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