Anthranilic Acid → Acetanthranil

HRID 1168560Notes

Reaction equation

HRID 1168560 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-ff7bda0ce75c4645a3019f833f207fa7
Source dataset
uspto-grants-2003_09
Patent number
US06624305B2

Reaction notes

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