Dimethylformamide → 3-(2-Chloropyridin-4-yloxy)isonicotinonitrile

HRID 911089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911089
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:16]=[N:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].[Cl:17][C:18]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][N:19]=1>O>[Cl:17][C:18]1[CH:23]=[C:22]([O:8][C:9]2[CH:16]=[N:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:21]=[CH:20][N:19]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 129590773-Hydroxypyridine-4-carbonitrile

Produkt 1

HCID 249946573-(2-Chloropyridin-4-yloxy)isonicotinonitrileAusbeute 0,82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A flask was charged with sodium hydride (3.99 g, 158 mmol) and DMF (50 mL), and 3-hydroxyisonicotinonitrile (15.8 g, 132 mmol) was added. The reaction was stirred for 2 hours at ambient temperature. 2-Chloro-4-nitropyridine (21.9 g, 138 mmol) was added and the reaction was and stirred overnight. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried and concentrated. The crude product was purified by silica gel chromatography, eluting with DCM, 5% ammoniated methanol in DCM to give the desired product (0.250 g, 0.820% yield) as yellow solid.

Aufarbeitung

  1. additionwas added
  2. stirringstirred overnight
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with DCM, 5% ammoniated methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-57c23413a42b472a8738bf88061f88f9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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