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Water → N-(3-[(5-Aminopyridin-2-yl)oxy]-4-chlorophenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 1800513
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1800513
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([C:19]#[N:20])([CH3:18])[CH3:17])[CH:11]=2)=[CH:4][C:3]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][N:24]=1.[Cl-].[Ca+2].[Cl-].O>C(O)C>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:21])[C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([C:19]#[N:20])([CH3:17])[CH3:18])[CH:11]=3)[CH:6]=[CH:7][C:2]=2[Cl:1])=[N:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 68418666N-{4-chloro-3-[(5-nitropyridin-2-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide

Produkt 1

HCID 68417569N-(3-[(5-Aminopyridin-2-yl)oxy]-4-chlorophenyl}-3-(1-cyano-1-methylethyl)benzamideAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of N-{4-chloro-3-[(5-nitropyridin-2--yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide (2.5 g, 5.72 mmol), calcium chloride (2.00 g, 17.2 mmol) and reduced iron (1.43 g, 25.7 mmol) in ethanol (35 mL)/water (5 mL) was stirred with heating at 90° C. for 4 hr. After the reaction mixture was cooled to room temperature, the insoluble material was filtered off through a pad filled with celite, and washed with ethyl acetate. The filtrate and the washing fluid were combined, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL), washed with water (50 mL×2), 5% aqueous sodium hydrogen carbonate solution (50 mL×2) and saturated brine (50 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (1.45 g, 62%) as a beige amorphous substance.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered off through a pad
  3. additionfilled with celite
  4. washwashed with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. additionThe obtained residue was diluted with ethyl acetate (100 mL)
  7. washwashed with water (50 mL×2), 5% aqueous sodium hydrogen carbonate solution (50 mL×2) and saturated brine (50 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)
  12. concentrationthe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3efedf82251b42f29e6c73c9012a2825
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

Notizen zur Reaktion

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