Anthranilic Acid → Acetanthranil

HRID 1858145Notes

Reaction equation

HRID 1858145 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-921af23940a8446cabb6a820917b9b71
Source dataset
uspto-grants-2000_11
Patent number
US06150523

Reaction notes

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