Dimethylformamide → 2H-Pyrido[4,3-d][1,3]oxazine-2,4(1H)-dione

HRID 268330Notes

Reaction equation

HRID 268330 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C([C:21]1[C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=[CH:23][CH:22]=1)(=O)N.C[N:31](C)[CH:32]=[O:33]>>[C:26]12[C:21](=[CH:22][CH:23]=[N:24][CH:25]=1)[NH:31][C:32](=[O:33])[O:29][C:27]2=[O:28]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 12014284-(Aminocarbonyl)-3-pyridinecarboxylic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 107970962H-Pyrido[4,3-d][1,3]oxazine-2,4(1H)-dione

Procedure

A 50 ml. flask was charged with 2.6 g. lead tetra-acetate suspended in 10 ml. dimethylformamide and stirred while a solution of 0.96 g. of 4-carbamylnicotinic acid in 5 ml. dimethylformamide was added dropwise during 10 minutes. The mixture was stirred for 10 minutes after completion of the addition, then poured onto 40 g. crushed ice. A precipitate of cream solids was collected by filtration, washed with water and dried in vacuo. The yield of 5-azaisatoic anhydride amounted to 0.68 g., melting point 180° with decomposition, and represented 72 percent of theory. On attempted purification by crystallization from organic solvents, extensive decomposition occurred. The structure was confirmed by elemental analysis, infra-red spectroscopy and mass spectrometry.

Workup

  1. additionflask was charged with 2.6 g
  2. additionafter completion of the addition
  3. additionpoured onto 40 g
  4. filtrationA precipitate of cream solids was collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. custompurification
  8. customby crystallization from organic solvents, extensive decomposition

Sources & evidence

ORD record
ord-85a3e3613309414b9e33e363e9dbe596
Source dataset
uspto-grants-1976_03
Patent number
US03947442

Reaction notes

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