Water → 2-Di-n-propylamino-8-(quinol-2-yl)-1,2,3,4-tetrahydronaphthalene

HRID 22139

Reaktionsgleichung

Reaktionsgleichung von HRID 22139
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[Mg].Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.O>C1COCC1.BrCCBr>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 119282-ChloroquinolineHCID 5462224MagnesiumHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 233735242-Di-n-propylamino-8-(quinol-2-yl)-1,2,3,4-tetrahydronaphthaleneAusbeute 181,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 78391,2-DibromoethaneKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1 g, 3.22 mmol) was added to a refluxing mixture of magnesium turnings (120 mg, 4.9 mmol) in 50 ml THF. Formation of the Grignard reagent was initiated by addition of 0.2 ml 1,2-dibromoethane (0.002 mmol). After 1.5 hours, 220 mg (0.33 mmol) Ni[PPh3 ]2Cl2 in 10 ml of THF were added followed by 800 mg (4.89 mmol) of 2-chloroquinoline. The solution continued to reflux for 15 minutes after which it was cooled, poured into water, and extracted three times with methalene chloride. The extract was dried with sodium sulfate and concentrated to obtain 2.1 g of a black oil. The crude was purified by using two flash columns. The first was eluted with 1:1 hexanes:ether and the second with 20:1 methylene chloride:methanol. 130 mg of the title compound were collected as product. Following crystallization in ethanol and water, 66 mg of solid were recovered, m.p. 82° C. Analysis: Theory (.1/3 H2O): C, 82.37; H, 8.48; N, 7.68; Found: C, 82.33; H, 8.44; N, 7.73.

Aufarbeitung

  1. temperatureto reflux for 15 minutes after which it
  2. temperaturewas cooled
  3. extractionextracted three times with methalene chloride
  4. dry with materialThe extract was dried with sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e52d946ba6b940f2adfefdb638da511e
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426226

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