Ammonia → 3-(Benzyloxy)-4-methoxyaniline

HRID 19983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19983
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([N+:31]([O-])=O)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24]C1C=CC=CC=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N>CO>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([NH2:31])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 127366801,2-Bis(benzyloxy)-4-nitrobenzene

Produkt 1

HCID 125477223-(Benzyloxy)-4-methoxyanilineAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium dithionite (2 g) was added to a solution of 3,4-Dibenzyloxy-1-nitro benzene (2.37 gm) in a mixture of methanol (30 ml)/aqueous ammonia (5 ml). After stirring for 12 hrs at room temperature, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (75 ml) and water (75 ml). The ethyl acetate layer was washed with water (25 ml), brine solution (25 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography over silica gel eluting with ethyl acetate/hexane (1:1) provided 1.0 g of 1-Benzyloxy-2-methoxy-5-aminobenzene (Yield=47%).

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (75 ml) and water (75 ml)
  3. washThe ethyl acetate layer was washed with water (25 ml), brine solution (25 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography over silica gel eluting with ethyl acetate/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d743163391f74bb3918b3ed78a729397
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745490B2

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