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

HRID 325036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325036
[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; 1M; 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-5390921ce5604507a4fc60d24bcec0d9
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221898B1

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