Ethyl Acetate → 3-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

HRID 718174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 718174
Br[C:2]1[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC(N(C)C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][C:2]2[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH:17]=[CH:16][N:15]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 904030533-Bromo-2-ethyl-6-nitropyridineHCID 178516507HCID 178516507, Verbindung

Produkt 1

HCID 904031083-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridineAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-Bromo-2-ethyl-6-nitropyridine (2.6 g, 11.3 mmol) and 2-chloro-4-hydroxypyridine (2.9 g, 22.5 mmol) were dissolved in DMA (20 mL). The solution was sonicated and sparged with Ar for 10 min. K2CO3 (4.7 g, 33.8 mmol) was added and the reaction mixture was stirred at 110° C. for 12 h. EtOAc (80 mL) was added and the suspension was washed with 10% K2CO3 (aq) (2×50 mL), 5% LiCl (aq) (2×50 mL), and brine (2×50 mL). The solution was dried (Na2SO4), concentrated in vacuo, and the resultant residue was purified by silica gel chromatography (EtOAc/hexanes) to afford 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.3 g, 37.2%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J=5.7 Hz, 1H), 8.25 (d, J=8.7 Hz, 1H), 7.96 (d, J=8.7 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.16 (dd, J=5.7, 2.3 Hz, 1H), 2.79 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 280.0 (M+H+).

Aufarbeitung

  1. customThe solution was sonicated
  2. customsparged with Ar for 10 min
  3. washthe suspension was washed with 10% K2CO3 (aq) (2×50 mL), 5% LiCl (aq) (2×50 mL), and brine (2×50 mL)
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe resultant residue was purified by silica gel chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-80804b49ebae47f68560a677484e00d9
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193719B2

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