Anthranilic Acid → Acetanthranil

HRID 1938805Notes

Reaction equation

HRID 1938805 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-4oxo-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-882725a6230247a6837c4af87574a96b
Source dataset
uspto-grants-1997_12
Patent number
US05693811

Reaction notes

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