2-Oxoglutaric Acid → (6,6-Dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij] quinolin-1-yl)Acetic Acid

HRID 351586

Reaktionsgleichung

Reaktionsgleichung von HRID 351586
Cl.[CH3:2][C:3]1([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6](N)[CH2:5][CH2:4]1.O=[C:16]([CH2:20][CH2:21]C(O)=O)[C:17]([OH:19])=[O:18]>C(O)(=O)C>[CH3:2][C:3]1([CH3:14])[C:12]2[C:7]3=[C:8]([C:20]([CH2:16][C:17]([OH:19])=[O:18])=[CH:21][N:6]3[CH2:5][CH2:4]1)[CH:9]=[CH:10][CH:11]=2

Komponenten

5

Edukt 3

HCID 512-Oxoglutaric AcidHCID 313Hydrochloric AcidHCID 225568373,4-dihydro-4,4-dimethyl-1-(2H)-quinolinamine

Produkt 1

HCID 22556735(6,6-Dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij] quinolin-1-yl)Acetic AcidAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of glacial acetic acid (80 mL) and concentrated hydrochloric acid (9 mL) was added 3,4-dihydro-4,4-dimethyl-1-(2H)-quinolinamine (9.5 g, 53.9 mmol) and 2-ketoglutaric acid (9.7 g, 65.1 mmol) and the suspension heated at reflux for 3 hours. After cooling the solvents were removed under reduced pressure and the residue dissolved in 500 mL of ethyl acetate. The ethyl acetate solution was washed with water (3×150 mL) and saturated aqueous sodium chloride (1×50 mL), dried over sodium sulfate,-filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 1-4% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 4.45 g (34%) of the desired compound as a tan foam. An impure fraction was extracted with 1N sodium hydroxice (2×50 mL) and the combined aqueous layers washed with diethyl ether (20 mL) and made acidic with concentrated hydrochloric acid (8 mL). This aqueous mixture was extracted with dichloromethane (2×100 mL), followed by drying (Na2SO4) to provide an additional 2.55 g (19%) of desired product

Aufarbeitung

  1. temperaturethe suspension heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the solvents
  4. customwere removed under reduced pressure
  5. dissolutionthe residue dissolved in 500 mL of ethyl acetate
  6. washThe ethyl acetate solution was washed with water (3×150 mL) and saturated aqueous sodium chloride (1×50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentration-filtered and concentrated under reduced pressure
  9. washeluting with 1-4% methanol in dichloromethane
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-810a0b9bc06a41b2be897756a6f3c268
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743785B2

Verknüpfte Notizen

Wird geladen…