Ethyl Acetate → Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 1791857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791857
[BH4-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-])=O)[CH:15]=2)=[CH:7][CH:6]=1)#[N:4].CCOC(C)=O>CCO.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:21][C:16]1[CH:15]=[C:14]([O:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)[CH:19]=[CH:18][C:17]=1[CH3:20]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 22033464[2-(4-Cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene

Produkt 1

HCID 22033532Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.127 g; 3.35 mmol) was added in portions to a cold suspension (ice:water temperature) of [2-(4-cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene (0.19 g; 0.67 mmol; from step (i) above) and aqueous copper sulfate (1.34 mL; 1 M; 1.34 mmol) in EtOH (5 mL) over five minutes. The temperature was allowed to rise to ambient and the stirring continued for 30 minutes. Addition of EtOAc (50 mL) and filtration through Celite afforded a clear solution that was washed with water, dried (K3CO3) and concentrated in vacuo. Flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 0.044 g (26%) of the sub-title compound as a white solid.

Aufarbeitung

  1. customafforded a clear solution that
  2. washwas washed with water
  3. customdried (K3CO3)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97967a60623a4f7b94a70e73c45afd80
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074820B2

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