Anthranilic Acid → 5-Methylisatoic anhydride

HRID 1282293Notes

Reaction equation

HRID 1282293 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](=[O:14])([O-])[O-].[Na+].[Na+].[C:17](Cl)(Cl)=O.C1(C)C=CC=CC=1>>[CH3:17][C:7]1[CH:8]=[C:2]2[C:1]([O:10][C:11](=[O:14])[NH:4][C:3]2=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 4

HCID 227Anthranilic AcidHCID 1140TolueneHCID 6371PhosgeneHCID 10340Sodium Carbonate

Product 1

HCID 2944785-Methylisatoic anhydride

Procedure

To an aqueous solution of anthranilic acid (100 g, 0.66 mol) and sodium carbonate (0.7 mol) a solution of phosgene in toluene (362 mL, 1.93 M, 0.7 mol) was added dropwise under vigorous stirring. The reaction becomes a suspension and is stirred for additional 8 hours and filtered. The residue was treated with aqueous Na2CO3 and filtered. Washed with water (4×150 mL) and dried.

Workup

  1. filtrationfiltered
  2. additionThe residue was treated with aqueous Na2CO3
  3. filtrationfiltered
  4. washWashed with water (4×150 mL)
  5. customdried

Sources & evidence

ORD record
ord-21a2314655264049836c6ae4857caed4
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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