Ethanol → 3-Azaisatoic anhydride

HRID 1459452Notes

Reaction equation

HRID 1459452 reaction equation
C[Si]([N:5]=[N+]=[N-])(C)C.[N:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([O:12][C:13]2=[O:18])=[O:11].C(O)C>C(Cl)(Cl)Cl>[NH:5]1[C:9]2[N:8]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13](=[O:18])[O:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 78378Azidotrimethylsilane

Product 1

HCID 109865823-Azaisatoic anhydride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trimethylsilylazide (89.1 ml) was added dropwise, with stirring, to a suspension of quinolinic anhydride (100.0 g) in dry chloroform (450 ml) under nitrogen. The mixture was stirred until nitrogen evolution had subsided (around 30 minutes) and then boiled under reflux with stirring for 45 minutes to give a solution. The mixture was cooled to ambient temperature and ethanol (40.0 ml) was added. The mixture was stirred for 20 minutes and a precipitate was collected by filtration and dried under vacuum overnight. The solid was stirred in cold acetonitrile (850 ml) and filtered. The filtrate was boiled under reflux for 15 minutes with stirring and then cooled in ice and filtered to give 4H-pyrido[2,3-d] [1,3]oxazine-2,4(1H)-dione, m.p. 213°-215° C. (with decomposition).

Workup

  1. custom(around 30 minutes)
  2. temperatureunder reflux
  3. stirringwith stirring for 45 minutes
  4. customto give a solution
  5. stirringThe mixture was stirred for 20 minutes
  6. filtrationa precipitate was collected by filtration
  7. customdried under vacuum overnight
  8. stirringThe solid was stirred in cold acetonitrile (850 ml)
  9. filtrationfiltered
  10. temperatureunder reflux for 15 minutes
  11. stirringwith stirring
  12. temperaturecooled in ice
  13. filtrationfiltered

Sources & evidence

ORD record
ord-737ae40734594d96a0ebad254ab85818
Source dataset
uspto-grants-1998_12
Patent number
US05854257

Reaction notes

Loading…