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

HRID 268330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268330
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]

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-85a3e3613309414b9e33e363e9dbe596
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03947442

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