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Sodium Iodide → 6'-methoxy-5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

HRID 2103088
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2103088
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][C:8]1([CH2:16][CH2:15][CH2:14]1)[CH2:7][CH2:6]2.Cl[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]([CH2:19][C:20]1[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=1)[C:8]1([CH2:14][CH2:15][CH2:16]1)[CH2:7][CH2:6]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 578035566'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

Produkt 1

HCID 690595946'-methoxy-5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]Ausbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] (270 mg), 2-(chloromethyl)quinoline (626 mg), K2CO3 (528 mg) and sodium iodide (30 mg) in acetone (20 mL) was refluxed over night. After evaporation of the solvent, water was added to the residue and the aqueous solution was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by column chromatography (10% ethyl acetate/hexane), giving 6′-methoxy-5′,7′-dimethyl-1′-(quinolin-2-ylmethyl)-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] as a light yellow solid (250 mg).

Aufarbeitung

  1. temperaturewas refluxed over night
  2. customAfter evaporation of the solvent, water
  3. additionwas added to the residue
  4. extractionthe aqueous solution was extracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by column chromatography (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ff324bebcda14148aef9d5450dd3042d
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07576094B2

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