2-Ethoxy-1-methoxy-4-nitro-benzene → 3-Ethoxy-4-methoxyaniline

HRID 1297103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297103
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[NH2:10])[CH3:2]

Komponenten

4

Edukt 1

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzene

Produkt 1

HCID 167919473-Ethoxy-4-methoxyanilineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Leave under hydrogen pressure (Patm) for 12 hours, 5 g of 2-ethoxy-1-methoxy-4-nitrobenzene (XIXaa), 500 mg of 10% palladium on charcoal (10% by weight of product to reduce), in 200 ml of methanol. Filter on celite, rinse several times with methanol. Evaporate to dryness. Take up in ether and evaporate. One obtains 3.28 g of the abovenamed product as a pinkish white powder. Yield: 79%. 1H-NMR (CDCl3, 300 MHz): d 1.46 (t, 3H, —CH3), 3.33 (s, 2H exchangeable, —NH2), 3.81 (s, 3H, OCH3), 4.05 (q, 2H, OCH2), 6.22(d, 1H Ar), 6.28 (dd, 1H Ar), 6.71 (d, 1H Ar).

Aufarbeitung

  1. customLeave under hydrogen pressure (Patm) for 12 hours
  2. filtrationFilter on celite
  3. washrinse several times with methanol
  4. customEvaporate to dryness
  5. customevaporate

Quellen und Nachweise

ORD-Eintrag
ord-70d9dd3c7c714b6dad0ba048af450658
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250410B2

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