Water → N-[5-(4-aminophenoxy)-2-methylphenyl]-3-(1-cyanocyclopropyl)benzamide

HRID 2190369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190369
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[C:9]([NH:11][C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH:15]=[CH:14][C:13]=2[CH3:28])=[O:10])[CH2:5][CH2:4]1)#[N:2].[Cl-].[Ca+2].[Cl-].O>C(O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:16]2[CH:15]=[CH:14][C:13]([CH3:28])=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:29]=[CH:30][CH:31]=[C:6]([C:3]4([C:1]#[N:2])[CH2:5][CH2:4]4)[CH:7]=3)[CH:17]=2)=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 673127463-(1-cyanocyclopropyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide

Produkt 1

HCID 67312290N-[5-(4-aminophenoxy)-2-methylphenyl]-3-(1-cyanocyclopropyl)benzamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 3-(1-cyanocyclopropyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide (3.19 g, 22.5 mmol), calcium chloride (5.55 g, 50 mmol) and reduced iron (14.5 g, 260 mmol) in ethanol (540 mL)/water (60 mL) was stirred with heating at 80° C. for 12 hr. The reaction mixture was cooled to room temperature, passed through a pad filled with celite to separate insoluble material, and the insoluble material was washed with ethanol. The filtrate and the washing were combined and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (400 mL), washed with 5% aqueous ammonium chloride solution (200 mL), water (200 mL×2), 5% aqueous sodium hydrogencarbonate solution (200 mL) and saturated brine (200 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (7.0 g, 84%) as a pale-yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionfilled with celite
  3. customto separate insoluble material
  4. washthe insoluble material was washed with ethanol
  5. concentrationconcentrated under reduced pressure
  6. additionThe obtained residue was diluted with ethyl acetate (400 mL)
  7. washwashed with 5% aqueous ammonium chloride solution (200 mL), water (200 mL×2), 5% aqueous sodium hydrogencarbonate solution (200 mL) and saturated brine (200 mL)
  8. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2cf65c6daa3448aab4d5772c4ec1a9cb
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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