Toluene → 1-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one

HRID 1244018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244018
C1(C)C=CC=CC=1.I[C:9]1([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10]1.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:30])[C:25](=[O:31])[CH2:24][CH2:23]2>C(=O)([O-])[O-].[Ag+2].C(OCC)(=O)C.CCCCCC>[CH3:30][N:26]1[C:27]2[C:22](=[CH:21][C:20]([O:19][C:9]3([S:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][CH2:10]3)=[CH:29][CH:28]=2)[CH2:23][CH2:24][C:25]1=[O:31]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 11000298(1-Iodocyclopropyl)(phenyl)sulfaneHCID 219318286-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 219318121-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-oneAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a dry toluene solution of [1-Iodo-cyclopropylsulfanyl]-benzene (375 mg, 1.36 mmol) was added 6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (200 mg, 1.13 mmol) and silver carbonate (312 mg, 1.13 mmol) under nitrogen and the reaction mixture was heated to 55° C. It took 3 more additions of the reagents to take the reaction to completion. The reaction was cooled to room temperature, filtered to remove the silver iodide and concentrated under vacuum to yield crude material. This was flash chromatograhed using 30% ethyl acetate/hexane to yield the title compound as a viscous oil (64 mg, 17% yield). 1H NMR (400 MHz, CDCl3) δ 1.31–1.33 (2H, m), 1.41–1.43 (2H, m), 2.59–2.62 (2H, m), 2.83–2.87 (2H, m), 3.31 (3H, s), 6.86–6.98 (4H, m), 7.20–7.31 (2H, m), 7.44–7.47 (2H, m). m/z (APCI+) 326 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 μM, 125×4 mm column), 6.59 minutes.

Aufarbeitung

  1. customthe reaction to completion
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. customto remove the silver iodide
  5. concentrationconcentrated under vacuum
  6. customto yield crude material

Quellen und Nachweise

ORD-Eintrag
ord-bf963116c7e54b6e8086ec5913dc2775
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119207B2

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