Dimethylformamide → 3-Azaisatoic anhydride

HRID 268314Notes

Reaction equation

HRID 268314 reaction equation
C([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=O)N.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:5]12[C:4](=[N:12][CH:11]=[CH:10][CH:9]=1)[NH:14][C:15](=[O:16])[O:8][C:6]2=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2588102-Carbamoylpyridine-3-carboxylic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 109865823-Azaisatoic anhydride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml. flask was charged with 2.0 g. 2-carbamylnicotinic acid* suspended in 20 ml. dimethylformamide. A 5.5 g. portion of lead tetra-acetate was added to the suspension, and the mixture was stirred at 50°-60° for 1 hour. The reaction mixture was poured into 20 ml. water; solids were separated by filtration, and 3-azaisatoic anhydride was recrystallized from dioxane, and dried in vacuo for 2 hours. The final yield of 3-azaisatoic anhydride amounted to 1.48 g., melting point 217°-219°, and represented 75 percent of theory. The structure was confirmed by elemental analysis and infrared spectroscopy.

Workup

  1. additionflask was charged with 2.0 g
  2. additionThe reaction mixture was poured into 20 ml
  3. customsolids were separated by filtration, and 3-azaisatoic anhydride
  4. customwas recrystallized from dioxane
  5. customdried in vacuo for 2 hours

Sources & evidence

ORD record
ord-f6310530d70a4347b4cd78c307285b6d
Source dataset
uspto-grants-1976_03
Patent number
US03947416

Reaction notes

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