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Ethanol → HCID 178510832, Verbindung

HRID 78120
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 78120
C(O)C.[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]#[N:20])=[N:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[OH:22][NH3+:23].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([NH:23][OH:22])=[NH:20])=[N:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 21645Hydroxylamine HClHCID 221813855-Benzyloxy-2-cyanomethylpyridine

Produkt 1

HCID 178510832HCID 178510832, VerbindungAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To an ethanol (30 mL) solution of (5-benzyloxy-pyridin-2-yl)-acetonitrile (1.77 g, 7.89 mmol) described in Manufacturing Example 127-1-4 were added hydroxylammonium chloride (848 mg, 11.8 mmol) and potassium carbonate (2.18 g, 15.8 mmol), which was stirred for 11 hours and 20 minutes at 70° C. The mixture was then stirred for another 5 hours and 45 minutes under reflux. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:1) to obtain the title compound (550 mg, 27%).

Aufarbeitung

  1. stirringThe mixture was then stirred for another 5 hours and 45 minutes
  2. temperatureunder reflux
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-1d333c4d82c24031895fb51fc7caa696
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841327B2

Notizen zur Reaktion

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