Triethylamine → 4-Acetyl-8-chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 2051344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2051344
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[C:7]([CH3:15])([CH3:14])[CH2:8][CH2:9][NH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:25](Br)(=[O:27])[CH3:26]>C(Cl)Cl>[C:25]([N:10]1[C:11]2[CH2:12][CH2:13][C:4]3[CH:3]=[C:2]([Cl:1])[CH:17]=[CH:16][C:5]=3[C:6]=2[C:7]([CH3:14])([CH3:15])[CH2:8][CH2:9]1)(=[O:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10482Acetyl bromideHCID 198331288-Chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Produkt 1

HCID 198331574-Acetyl-8-chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

10.6 g (0.043 mol) of 8-chloro-1,1-dimethyl -1,2,3,4,5,6-hexahydrobenzo[f]quinoline and 6.6 ml (0.047 mol) of triethylamine are dissolved in 100 ml of methylene chloride and 3.5 ml (0.047 mol) of acetyl bromide dissolved in 20 ml of methylene chloride are added dropwise thereto at 0°. After stirring for 1 hour, the mixture is extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Recrystallization from methylene chloride/ hexane gives 4-acetyl-8-chloro-1,1-dimethyl-1,2,3,4,5,6hexahydrobenzo[f]quinoline as white crystals with melting point 126-127°.

Aufarbeitung

  1. additionare added dropwise
  2. customat 0°
  3. extractionthe mixture is extracted with methylene chloride/water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent is distilled in a vacuum
  6. customRecrystallization from methylene chloride/ hexane

Quellen und Nachweise

ORD-Eintrag
ord-64e278da835c4172b5f5c81b9aed497f
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017608

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