Anthranilic Acid → Isatoic Anhydride

HRID 650464Notes

Reaction equation

HRID 650464 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[C:13]([OH:22])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH2:16]>C1COCC1>[C:14]12[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:16][C:2](=[O:4])[O:22][C:13]2=[O:21]

Participants

4

Reactant 2

HCID 227Anthranilic Acid2×HCID 94429Triphosgene

Product 1

HCID 8359Isatoic AnhydrideYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An ice-cold solution of triphosgene (3.0 g, 10 mmol, 0.4 eq) in 10 mL of anhydrous THF was added to a mixture or solution of anthranilic acid (or 2-amino-benzoic acid) (25 mmol) in 15 mL of dry THF and cooled slowly. The mixture as then stirred or shaken for 24-48 h at room temperature nd cooled in a refrigerator (0° C. to −10° C.) for 12-24 h. The resulting solid was collected by filtration and washed with cold methyl t-butyl ether (MTBE) and dried to give the isatoic anhydride in 70-98% yield. About 30 isatoic anhydrides were prepared in this manner.

Workup

  1. temperaturecooled slowly
  2. stirringshaken for 24-48 h at room temperature
  3. temperaturecooled in a refrigerator (0° C. to −10° C.) for 12-24 h
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with cold methyl t-butyl ether (MTBE)
  6. customdried

Sources & evidence

ORD record
ord-b1fe1adddb82405ba4e0b9c73d217ae7
Source dataset
uspto-grants-2001_08
Patent number
US06274383B1

Reaction notes

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