Phosgene → 8-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 635514Notes

Reaction equation

HRID 635514 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH2:12].[C:13](Cl)(Cl)=[O:14]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]2[C:6]([O:8][C:13](=[O:14])[NH:12][C:4]=12)=[O:7]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dioneYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 10.0 g (60.0 mmol) of 3-methoxyanthranilic acid in 60 mL of 1,4-dioxane was slowly added 100 mL (193 mmol) of a 1.93 molar solution of phosgene in toluene, at room temperature. The mixture was stirred overnight. The mixture was concentrated to yield a residue which was triturated with ethyl acetate-hexane (1:4), filtered, washed with hexane and dried to afford 11.33 g (98%) of the 3-methoxyisatoic anhydride as an off white solid. MS (Cl mode) m/z 176 (M-18, 100%), 194 (M+H, 53%).

Workup

  1. customat room temperature
  2. concentrationThe mixture was concentrated
  3. customto yield a residue which
  4. customwas triturated with ethyl acetate-hexane (1:4)
  5. filtrationfiltered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-8dd9118f5f064edab6ca1f9e421d7b50
Source dataset
uspto-grants-2001_02
Patent number
US06187923B1

Reaction notes

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