Anthranilic Acid → Acetanthranil

HRID 1795393Notes

Reaction equation

HRID 1795393 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)C)(=O)[CH3:12]>>[CH3:11][C:12]1[O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1

Participants

3

Reactant 2

HCID 227Anthranilic AcidHCID 7918Acetic Anhydride

Product 1

HCID 68236Acetanthranil

Procedure

Anthranilic acid (274.3 g) and acetic anhydride (1.1 L) were combined then heated at reflux for 3.5 hours. The reaction mixture was concentrated under vacuum. The residue was combined with methanol (550 mL) then concentrated under vacuum to provide 2-methyl-4-oxo-3,1-benzoxazine as a brown oil.

Workup

  1. temperatureat reflux for 3.5 hours
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-fd21f89d9a5744df93bf7ccf3adb14d7
Source dataset
uspto-grants-2006_04
Patent number
US07026482B2

Reaction notes

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