Potassium Carbonate → 3-(1-cyanocyclopropyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

HRID 1800450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800450
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:13]1([C:16]2[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[C:19]([NH:21][C:22]2[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=2[CH3:29])=[O:20])[CH2:15][CH2:14]1)#[N:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:11]([C:13]1([C:16]2[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[C:19]([NH:21][C:22]2[CH:27]=[C:26]([O:28][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=3)[CH:25]=[CH:24][C:23]=2[CH3:29])=[O:20])[CH2:15][CH2:14]1)#[N:12]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 673125693-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide

Produkt 1

HCID 684197213-(1-cyanocyclopropyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamideAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-chloro-5-nitropyridine (3.25 g, 20.5 mmol) and 3-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide (6.0 g, 20.5 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (7.08 g, 51.3 mmol), and the mixture was stirred at 60° C. for 12 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with water (300 mL), 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70). The obtained solution was concentrated under reduced pressure to give the title compound (8.8 g, quantitative) as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate (300 mL)
  4. washwashed with water (300 mL), 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70)
  9. concentrationThe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55c11d7dc66048daadd606b5ee5aeb6c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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