Diethyl Ether → Ethyl 1-quinazolin-4-ylindol-3-ylacetate

HRID 597040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597040
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12]2)=[N:3][CH:2]=1.C(OCC)C>[Pd].C1(OC2C=CC=CC=2)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2)=[N:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 54457736Ethyl 1-quinazolin-4-ylindolin-3-ylacetate

Produkt 1

HCID 21449394Ethyl 1-quinazolin-4-ylindol-3-ylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A mixture of ethyl 1-quinazolin-4-ylindolin-3-yl-acetate (2.6g.) and 10% w/w palladium on charcoal catalyst (1.3g.) in diphenyl ether (20ml.) was heated under reflux for 30 minutes. The mixture was cooled to room temperature, mixed with diethyl ether (50ml.) and filtered through diatomaceous earth. The solid residue was washed with diethyl ether (50ml.). The combined diethyl ether solution was evaporated in vacuo, and the residue was chromatographed on silica gel (ca 150g.) using, as eluant, petroleum ether (b.p. 40°-60° C.) containing an increasing proportion of diethyl ether. Diphenyl ether was recovered from the first fractions (rich in petroleum ether). Evaporation in vacuo of later fractions gave a syrup which crystallised from a mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.) to give ethyl 1-quinazolin-4-ylindol-3-ylacetate, m.p. 65°-67° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationfiltered through diatomaceous earth
  4. washThe solid residue was washed with diethyl ether (50ml.)
  5. customThe combined diethyl ether solution was evaporated in vacuo
  6. customthe residue was chromatographed on silica gel (ca 150g.)
  7. additionpetroleum ether (b.p. 40°-60° C.) containing an increasing proportion of diethyl ether
  8. customDiphenyl ether was recovered from the first fractions (rich in petroleum ether)
  9. customEvaporation in vacuo of later fractions
  10. customgave a syrup which
  11. customcrystallised from a mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-9b3c1d080fc64c2194dfd807913febf8
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012513

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