Water → HCID 67854261, Verbindung

HRID 1587839

Reaktionsgleichung

Reaktionsgleichung von HRID 1587839
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:4][CH:3]=1.C[CH2:23][CH2:24][C:25]([CH2:27][C:28]([O-])=[O:29])=O.O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:24]([C:25]1[CH2:27][C:28](=[O:29])[C:3]2[C:2](=[CH:21][CH:20]=[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:10](=[O:19])[C:11]4=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]4[C:13]3=[O:14])[CH:4]=2)[N:1]=1)[CH3:23]

Komponenten

6

Edukt 3

HCID 962WaterHCID 9433661H-Isoindole-1,3(2H)-dione, 2-[2-(4-aminophenoxy)ethyl]-HCID 119662643-Oxohexanoate

Produkt 1

HCID 67854261HCID 67854261, VerbindungAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of N-(2-(4-aminophenoxy)ethyl)phthalimide (4.2 g), methylpropionylacetate (1.94 g) and p-toluenesulphonic acid (100 mg) in benzene (95 ml) was stirred and heated at reflux for 3 hours with azeotropic removal of water. Volatile material was then removed by evaporation and the residue was added to a refluxing eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (25 ml). The mixture was heated at reflux for 15 minutes and then cooled to ambient temperature. Hexane (80 ml) was added to the mixture which was triturated to give a solid. The solid was collected by filtration and washed with hexane. Ethyl acetate (70 ml) was added to the solid and the mixture was heated at reflux for 5 minutes and then cooled in an ice-bath. The undissolved solid was collected by filtration and washed with ethyl acetate to give 2-ethyl-6-(2-phthalimidoethoxy)-4-quinolone (2.5 g) as an off white solid, m.p. 168°-171° C.; NMR (d6 -DMSO): 1.24(t, 3H), 2.59(q, 2H), 4.0(t, 2H), 4.28(t, 2H), 5.87(s, 1H), 7.18(dd, 1H), 7.45(m, 2H), 7.84(m, 4H), 11.4(br s, 1H).

Aufarbeitung

  1. temperatureheated
  2. customVolatile material was then removed by evaporation
  3. additionthe residue was added to a refluxing eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (25 ml)
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 15 minutes
  6. additionHexane (80 ml) was added to the mixture which
  7. customwas triturated
  8. customto give a solid
  9. filtrationThe solid was collected by filtration
  10. washwashed with hexane
  11. additionEthyl acetate (70 ml) was added to the solid
  12. temperaturethe mixture was heated
  13. temperatureat reflux for 5 minutes
  14. temperaturecooled in an ice-bath
  15. filtrationThe undissolved solid was collected by filtration
  16. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-50c2258451af4943aa2c9d74ba08049a
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219863

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