Methane → 6,9-Difluorobenzo[g]isoquinoline-5,10-dione

HRID 440352

Reaktionsgleichung

Reaktionsgleichung von HRID 440352
[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[C:4]([C:6]1[C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=[CH:8][CH:7]=1)=[O:5].FC1C=CC(F)=CC=1C(C1C=NC=CC=1C(O)=O)=O.C1COCC1.C>OS(O)(=O)=O.O=S(=O)=O>[F:1][C:2]1[C:3]2[C:4](=[O:5])[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[C:12](=[O:14])[C:15]=2[C:16]([F:19])=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 297MethaneHCID 8028TetrahydrofuranHCID 100156123-(2,5-Difluorobenzoyl)isonicotinic acidHCID 104679084-(2,5-Difluorobenzoyl)nicotinic acid

Produkt 1

HCID 101059046,9-Difluorobenzo[g]isoquinoline-5,10-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24681Fuming sulfuric acidLösungsmittel2×

Versuchsvorschrift

A solution of the mixture of 4-(2,5-difluorobenzoyl)nicotinic acid and 3-(2,5-difluorobenzoyl)isonicotinic acid of Preparative Example 2 (61.07 g) in 20% oleum (100 mL) is heated at 140° C. while 20% oleum is added in four portions (13.2 mL each) at 20 min-intervals. After the fourth addition the mixture is heated for 20 min, then it is cooled to room temperature and quenched with a mixture of ice (1,500 g), water (1,500 mL) and 35% NaOH (350 mL). The mixture is extracted four times with methylene chloride (1×1,000 mL followed by 3×500 mL). The combined organic solutions are washed with water (2×1,000 mL), dried (Na2SO4) and the solvent removed by roto-evaporation. The dark-red solid obtained (56.0 g) is dissolved in boiling THF (840 mL) and decolorizing charcoal (8.40 g) is added. After 30 min the mixture is filtered while hot and the filtrate concentrated to 200 mL. The precipitate obtained is collected by suction filtration to give 6,9-difluorobenzo[g]isoquinoline-5,10-dione (43.00 g).

Aufarbeitung

  1. additionis added in four portions (13.2 mL each) at 20 min-intervals
  2. additionAfter the fourth addition the mixture
  3. temperatureis heated for 20 min
  4. customquenched with a mixture of ice (1,500 g), water (1,500 mL) and 35% NaOH (350 mL)
  5. extractionThe mixture is extracted four times with methylene chloride (1×1,000 mL followed by 3×500 mL)
  6. washThe combined organic solutions are washed with water (2×1,000 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed by roto-evaporation
  9. customThe dark-red solid obtained (56.0 g)
  10. dissolutionis dissolved
  11. additionis added
  12. filtrationAfter 30 min the mixture is filtered while hot and the filtrate
  13. concentrationconcentrated to 200 mL
  14. customThe precipitate obtained
  15. filtrationis collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-c642b2ee49c04a59be95c26656dc75ce
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519029

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