Ethylene Glycol → HCID 67241257, Verbindung

HRID 217901

Reaktionsgleichung

Reaktionsgleichung von HRID 217901
[O:1]=[C:2]1[C:11](=[O:12])[C:10]2[N:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:5]=2[C:4]2[NH:21][C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:23][C:3]1=2.[CH2:28](O)[CH2:29][OH:30].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:12]=[C:11]1[C:10]2[N:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:5]=2[C:4]2[NH:21][C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:23][C:3]=2[C:2]21[O:30][CH2:29][CH2:28][O:1]2

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 4514692,7,9-Trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

Produkt 1

HCID 67241257HCID 67241257, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A suspension of trimethyl 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate, 1 (1.2 g, 3.22 mMol) in benzene (200 mL) was treated with ethylene glycol (10 mL) and p-toluensulfonic acid (60 mg, 0.32 mMol). The resulting mixture was heated at reflux under a Dean-Stark trap and reflux condenser for 14 hours. The orange suspension became a yellow solution. The heat was turned off, the trap was removed, and the condenser was replaced. To the hot solution, a mixture of benzene (75 mL) and DCM (75 mL) was cautiously added. The resulting solution was allowed to cool to room temperature, and then washed with 5% aqueous NaHCO3 (100 mL). The organic layer was separated and washed with water (100 mL). The organic layer was separated, dried over Na2SO4, and filtered. Evaporation of solvent at reduced pressure gave a yellow solid. Flash chromatography on silica gel (40 g), eluting with EtOAc-DCM-Hexane (50:25:25) gave purified 2 (1/02 g, 74.4%) as a yellow solid upon evaporation of solvent. 1H-NMR (CDCl3, δ) 12.31 (s, 1H, NH), 8.77 (s, 1H, H-8), 7.15 (d, 1H, H-3), 4.35 (m, 2H, OCH2), 4.30 (m, 2H, OCH2), 4.11 (s, 1H, CO2CH3), 4.07 (s, 1H, CO2CH3), 3.93 (s, 1H, CO2CH3).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under a Dean-Stark trap
  3. temperaturereflux condenser for 14 hours
  4. customthe trap was removed
  5. additionTo the hot solution, a mixture of benzene (75 mL) and DCM (75 mL)
  6. additionwas cautiously added
  7. washwashed with 5% aqueous NaHCO3 (100 mL)
  8. customThe organic layer was separated
  9. washwashed with water (100 mL)
  10. customThe organic layer was separated
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customEvaporation of solvent at reduced pressure
  14. customgave a yellow solid
  15. washFlash chromatography on silica gel (40 g), eluting with EtOAc-DCM-Hexane (50:25:25)
  16. customgave
  17. custompurified 2 (1/02 g, 74.4%) as a yellow solid
  18. customupon evaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-9c35a81b2af1481cb160b86a2d7672c4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198290B2

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