Anthranilic Acid → Acetanthranil

HRID 1862020Notes

Reaction equation

HRID 1862020 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-e2fb55d1443d4341b367173f0c07e7d4
Source dataset
uspto-grants-2003_03
Patent number
US06534654B2

Reaction notes

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