Dimethylformamide → Isatoic Anhydride

HRID 268313Notes

Reaction equation

HRID 268313 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)C(N)=O.C[N:14](C)[CH:15]=[O:16].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>O>[C:2]12[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH:14][C:15](=[O:16])[O:12][C:1]2=[O:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6957Phthalamic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 8359Isatoic Anhydride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml. flask was charged with 2.0 g. phthalamic acid suspended in 20 ml. dimethylformamide at room temperature. A 5.4 g. portion of lead tetra-acetate was added to the suspension, and the reaction mixture was held at room temperature for 40 minutes. The reaction mixture was poured into 30 ml. water. Isatoic anhydride was filtered from the water, recrystallized from dioxane, and dried in vacuo for 2 hours. The final yield of isatoic anhydride amounted to 1.07 g. tan solids, melting point 243°, and represented 54 percent of theory based on the phthalamic acid.

Workup

  1. additionflask was charged with 2.0 g
  2. customat room temperature
  3. additionThe reaction mixture was poured into 30 ml
  4. filtrationIsatoic anhydride was filtered from the water
  5. customrecrystallized from dioxane
  6. customdried in vacuo for 2 hours

Sources & evidence

ORD record
ord-8509c51d2327474884dcb24775a06e1b
Source dataset
uspto-grants-1976_03
Patent number
US03947416

Reaction notes

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