Hydrazine → 2-Methoxy-2'-amino-4,4'-dibromobiphenyl

HRID 71907

Reaktionsgleichung

Reaktionsgleichung von HRID 71907
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:4]([O:18][CH3:19])[CH:3]=1.NN>C(O)C.[Ru]>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[O:18][CH3:19])=[C:9]([NH2:15])[CH:10]=1

Komponenten

5

Edukt 2

HCID 9321HydrazineHCID 99774712-Methoxy-2'-nitro-4,4'-dibromobiphenyl

Produkt 1

HCID 99984202-Methoxy-2'-amino-4,4'-dibromobiphenylAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23950RutheniumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a suspension of 4,4′-dibromo-2-methoxy-2′-nitro-biphenyl (3.76 g, 9.8 mmol) and 5% Ru/C (400 mg) in ethanol (37 ml) at 65-70° C. was added dropwise a solution of hydrazine (4.6 ml, 59 mmol) in ethanol (5 ml). The mixture was refluxed for 7 hours and filtered through a pad of CELITE. The CELITE pad was washed with ethanol. The combined solution was concentrated under reduced pressure. Coevaporation with ethanol, EtOAc and DCM gave 4,4′-dibromo-2′-methoxy-biphenyl-2-ylamine as yellow solid (3.5 g).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 7 hours
  2. filtrationfiltered through a pad of CELITE
  3. washThe CELITE pad was washed with ethanol
  4. concentrationThe combined solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b20646e410e74b57b9aedcd41fff593a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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