Tetramethoxysilane → 8-Chloro-1,1-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolin-3-one

HRID 1639377

Reaktionsgleichung

Reaktionsgleichung von HRID 1639377
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[CH3:13][C:14]([CH3:19])=[CH:15][C:16]([NH2:18])=[O:17].CO[Si](OC)(OC)OC.[F-].[Cs+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3[C:14]([CH3:19])([CH3:13])[CH2:15][C:16](=[O:17])[NH:18][C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 12682TetramethoxysilaneHCID 20560Senecioic acid amideHCID 25953Cesium fluorideHCID 44561396-Chloro-2-tetralone

Produkt 1

HCID 543287808-Chloro-1,1-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 127 g (0.7 mol) of 6-chloro-2-tetralone, 70.0 g (0.7 mol) of 3,3-dimethylacrylamide, 63.6 ml (0.42 mol) of tetramethoxysilane and 85.3 g (0.56 mol) of cesium fluoride in 400 ml of toluene is boiled under reflux for 18 hours. Distillation of the solvent in a vacuum, extraction with methylene chloride/water, chromatography on silica gel with ethyl acetate/hexane (1:1) and recrystallization from methylene chloride/hexane yields 8-chloro-1,1-dimethyl-1,2,5,6-tetrahydrobenzo[f]-quinolin-3-one as white crystals with melting point 213°.

Aufarbeitung

  1. temperatureunder reflux for 18 hours
  2. distillationDistillation of the solvent
  3. extractionin a vacuum, extraction with methylene chloride/water, chromatography on silica gel
  4. customwith ethyl acetate/hexane (1:1) and recrystallization from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-39b1ec7db3924361b20b3a6b56eab709
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883815

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