Anthranilic Acid → 2-Ethyl-benzo[d][1,3]oxazin-4-one

HRID 2386922Notes

Reaction equation

HRID 2386922 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](OC(=O)CC)(=O)[CH2:12][CH3:13]>>[CH2:12]([C:13]1[O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1)[CH3:11]

Participants

3

Reactant 2

HCID 227Anthranilic AcidHCID 31263Propionic anhydride

Product 1

HCID 9285262-Ethyl-benzo[d][1,3]oxazin-4-oneYield 98%

Conditions

Temperature
130 °C

Procedure

Anthranilic acid (10 g, 72.9 mmol) and propionic anhydride (20.9 g, 160 mmol) were mixed and stirred at 130° C. for 2 hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in methylene chloride, the organic phase was washed with saturated sodium hydrogen carbonate aqueous solution and then distilled water and dried with anhydrous sodium sulfate. The target compound (12.5 g, 98%) was obtained as a colorless solid by filtering off the sodium sulfate and concentrating to dryness.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe organic phase was washed with saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialdistilled water and dried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-43e00bf2b210439ba439bba4f9de634a
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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