4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene → 5-(methylsulfonyl)-2-[(1E)-prop-1-en-1-yl]aniline

HRID 2390156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390156
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([N+:14]([O-])=O)[CH:6]=1)(=[O:4])=[O:3]>CC(O)=O.[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([CH:6]=1)[NH2:14])(=[O:3])=[O:4]

Komponenten

4

Edukt 1

HCID 585219844-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene2×

Produkt 1

HCID 585220135-(methylsulfonyl)-2-[(1E)-prop-1-en-1-yl]anilineAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene (Intermediate 59; 1.10 g; 4.56 mmol) in AcOH (7 ml) was treated with powdered iron (3.82 g; 68.4 mmol) and the reaction mixture was stirred at 90° C. for 25 min. Further AcOH was added (20 mL), the solid was filtered off and rinsed with EtOAc. The solvents were removed under reduced pressure, the residue was taken up in EtOAc and washed with saturated NaHCO3 solution twice the with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil (784 mg, 81%).

Aufarbeitung

  1. filtrationthe solid was filtered off
  2. washrinsed with EtOAc
  3. customThe solvents were removed under reduced pressure
  4. washwashed with saturated NaHCO3 solution twice the with brine
  5. customThe organic phase was dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55328cad460c4d87b5cd0170de8399c1
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273769B2

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