Sodium Hydroxide → 5-Bromopyridine-2-carbonitrile

HRID 72394

Reaktionsgleichung

Reaktionsgleichung von HRID 72394
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH2:15])=O)=[N:11][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:15])=[N:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7351515-Bromopyridine-2-carboxamide

Produkt 1

HCID 8171545-Bromopyridine-2-carbonitrileAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (111 g, 0.720 mol) was added to a mixture of 5-bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300 ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1. Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1
  8. customCollected fractions, after solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e83cf6404d21478aac0b005324c1ef0e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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