2-Chloroisoquinoline → 2-Phenylisoquinoline

HRID 1795385

Reaktionsgleichung

Reaktionsgleichung von HRID 1795385
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[N:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1>C1COCC1>[C:1]1([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 219893902-ChloroisoquinolineHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 53205292-PhenylisoquinolineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of phenylmagnesium bromide (1M in THF, 3.6 mL, 3.6 mmol) is added to a solution of 2-chloro-isoquinoline (258 mg, 1.57 mmol)) and Fe(acac)3 (28 mg, 0.078 mmol) in THF (10 mL) at −30° C. After stirring for 50 min at that temperature, the reaction is quenched with brine, the aqueous layer is extracted with Et2O, the combined organic phases are dried over Na2SO4 and evaporated, and the residue is purified by flash chromatography (hexane/ethyl acetate, 10:1). After eluting a first fraction containing biphenyl (60 mg), one obtains 2-phenyl-isoquinoline as a colorless solid (184 mg, 57%). 1H NMR (300 MHz, CD2Cl2) δ 8.60 (d, 1H), 8.11 (d, 1H), 7.91 (d, 1H), 7.66–7.72 (m, 4H), 7.48–7.57 (m, 4H); 13C NMR (75 MHz, CD2Cl2) δ 160.9, 142.6, 140.1, 137.2, 130.3, 130.2, 128.8, 128.5, 127.7, 127.5, 127.3, 127.0, 120.1.

Aufarbeitung

  1. customthe reaction is quenched with brine
  2. extractionthe aqueous layer is extracted with Et2O
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customthe residue is purified by flash chromatography (hexane/ethyl acetate, 10:1)
  6. washAfter eluting a first fraction
  7. additioncontaining biphenyl (60 mg), one

Quellen und Nachweise

ORD-Eintrag
ord-568248c7f9ff402b803e549a0741a8cc
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026478B2

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