8-Hydroxyquinoline → HCID 21783328, Verbindung

HRID 1846744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846744
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=1)([O-:3])=[O:2]

Komponenten

9

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 1458133-Nitropyrrole

Produkt 1

HCID 21783328HCID 21783328, VerbindungAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-nitropyrrole (270 mg, 2.41 mmol), iodobenzene (0.267 mL, 2.39 mmol), 8-hydroxyquinoline (60 mg, 0.41 mmol) and K2CO3 (600 mg, 4.34 mmol) in DMSO (3 mL) was degassed with argon before being charged with CuI (45 mg, 0.23 mmol). The mixture in a sealed tube was heated at 130 C for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 3-nitro-1-phenyl-1H-pyrrole (410 mg).

Aufarbeitung

  1. customwas degassed with argon
  2. temperatureThe mixture in a sealed tube was heated at 130 C for 20 h
  3. customThe organic phase was separated
  4. washwashed with 1N HCl
  5. dry with materialwith 5% NaHCO3, dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5758e3d60d5f486dbdf42beaccb8ab53
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952027B2

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