Potassium Carbonate → 2,6-Dimethyl-5-nitroquinoline

HRID 2088469

Reaktionsgleichung

Reaktionsgleichung von HRID 2088469
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.[C:16]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 179891062-Chloro-6-methyl-5-nitroquinoline

Produkt 1

HCID 7665652,6-Dimethyl-5-nitroquinolineAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of 2-chloro-6-methyl-5-nitro-quinoline (350 mg, 1.57 mmol) in dioxane (6.7 mL) and water (0.7 mL) were added K2CO3 (652 mg, 4.72 mmol), trimethylboroxine (0.22 mL, 1.57 mmol) and PdCl2(dppf) (129 mg, 0.157 mmol) under Ar. The mixture was heated at 105° C. overnight, then cooled and the resulting solid was collected by filtration, washed with ethyl acetate, and dried. Purification by flash column (hexane/ethyl acetate gradient) gave 2,6-dimethyl-5-nitro-quinoline (195 mg, 61%).

Aufarbeitung

  1. temperaturecooled
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried
  5. customPurification by flash column (hexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3eeba92cbac94ff5b6dcd2799c8dd6b2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435990B2

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