1-(Bromoacetyl)-1,2,3,4-tetrahydroquinoline → 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

HRID 597706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597706
[Cl-].[Al+3].[Cl-].[Cl-].Br[CH2:6][C:7]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)=[O:8]>O>[CH2:6]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][CH2:10][N:9]3[C:7]1=[O:8]

Komponenten

4

Edukt 2

HCID 5838141-(Bromoacetyl)-1,2,3,4-tetrahydroquinolineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 149184935,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

To a flask containing 30 g. of aluminum chloride is added 20.5 g. of 1-(bromoacetyl)-1,2,3,4-tetrahydroquinoline. After a vigorous initial reaction, the mixture is heated to 200° C. After 30 minutes, the reaction mixture is poured on cold water and the resulting oil is extracted with methylene chloride, dried, and the solvent removed under reduced pressure. The resultant oil is dissolved in ether, the solution cooled and the precipitate sublimed to yield 1,2,5,6-tetrahydro-4H-pyrrolo-(3,2,1-ij)quinolin-2-one, m.p. 90°-93° C.

Aufarbeitung

  1. additionTo a flask containing 30 g
  2. customAfter a vigorous initial reaction
  3. extractionthe resulting oil is extracted with methylene chloride
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe resultant oil is dissolved in ether
  7. temperaturethe solution cooled

Quellen und Nachweise

ORD-Eintrag
ord-63d37c1c4e094998a15253534f1ef93c
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04015005

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