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Water → 1-(4-chlorophenyl)-8,9-dihydro-7-methylene-7H-pyrrolo[3,2,1-ij]quinoline

HRID 263426
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Reaktionsgleichung

Reaktionsgleichung von HRID 263426
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:24]3=[C:25]4[C:20]([C:21](=O)[CH2:22][CH2:23]3)=[CH:19][CH:18]=[CH:17][N:16]4[CH:15]=2)=[CH:10][CH:9]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:24]3=[C:25]4[C:20]([C:21](=[CH2:1])[CH2:22][CH2:23]3)=[CH:19][CH:18]=[CH:17][N:16]4[CH:15]=2)=[CH:10][CH:9]=1
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Komponenten

6

Edukt 3

HCID 962WaterHCID 190380211-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin-7-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 190380201-(4-chlorophenyl)-8,9-dihydro-7-methylene-7H-pyrrolo[3,2,1-ij]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysator
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Methyltriphenylphosphonium bromide (3.8 g) was added to 25 ml of anhydrous tetrahydrofuran. To this mixture was added the solution of potassium t-butoxide (1.2 g) in 25 ml of tetrahydrofuran at ambient temperature. After stirring for 3 hours, to this solution was added the solution of 1-(4-chlorophenyl)-8,9-dihydro-7H-pyrrolo[3,2,1-ij]quinolin-7-one (1.5 g), which was obtained in example 2, in 15 ml of tetrahydrofuran. After stirring for 30 min., to this solution was added water and extracted with ethyl acetate. The organic solution was washed with brine and dried over anhydrous sodium sulfate. After removing drying agent by filtration and organic solvent by evaporation under reduced pressure, the residue was purified by alumina column chromatography, and the title compound was obtained as yellow crystals (1.1 g) .

Aufarbeitung

  1. stirringAfter stirring for 30 min., to this solution
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing
  6. customdrying agent
  7. filtrationby filtration and organic solvent
  8. customby evaporation under reduced pressure
  9. customthe residue was purified by alumina column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-35a96525160248209cc22e79df0949ea
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05643920

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