Sodium Hydroxide → 5-Amino-6-bromo-2-pyridinecarbonitrile

HRID 400574

Reaktionsgleichung

Reaktionsgleichung von HRID 400574
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br:10]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][C:7]=1[Br:10]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 38713955-Aminopyridine-2-carbonitrile

Produkt 1

HCID 242138925-Amino-6-bromo-2-pyridinecarbonitrileAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

5-Aminopyridine-2-carbonitrile (2.38 g, 20 mmol) was dissolved in 6 mL of glacial acetic acid. A solution of bromine (1 mL, 20 mmol) in 2.5 mL of glacial acetic acid was added dropwise over a period of 30 minutes while the room temperature was maintained with a water bath. The resulting slurry was stirred for 1 hour at room temperature, treated with 50 mL of aqueous 20% sodium hydroxide solution and extracted with three 160 mL portions of dichloromethane. The combined organic layers were dried over sodium sulfate (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by crystallization from ethyl acetate-hexanes to give 5-amino-6-bromopyridine-2-carbonitrile (1.42 g, 35% yield).

Aufarbeitung

  1. temperaturewas maintained with a water bath
  2. extractionextracted with three 160 mL portions of dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by crystallization from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3f12eec8677b4ebf8019de91e1881cd1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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