Ethyl Acetate → 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

HRID 15513

Reaktionsgleichung

Reaktionsgleichung von HRID 15513
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17](=[O:19])[CH3:18])=[C:11]([N+:20]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+].CCOC(C)=O>C1(C)C=CC=CC=1.O.[Fe]>[NH2:20][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[C:17](=[O:19])[CH3:18]

Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

Produkt 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone (3.6 g, 12 mmol), iron powder (4.5 g) and ammonium formate (5.5 g) in toluene (50 mL) and water (50 mL) was heated at reflux temp. for 2 days with stirring. To this mixture was added EtOAc (100 mL), stirred for 20 minutes, the solid was filtered through a celite bed and washed with EtOAc (150 mL). The EtOAc layer was separated from the filtrate solution, washed with water (2×100 mL), dried over MgSO4 and concentrated in vacuo to afford the product (2.80 g, 86%) as a beige-colored solid. 1H NMR (CDCl3) δ 7.41-7.30 (m, 5H), 7.13 (s, 1H), 6.15 (br s, 2H), 6.10 (s, 1H), 5.13 (s, 2H), 3.84 (s, 3H), 2.51 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temp
  3. stirringstirred for 20 minutes
  4. filtrationthe solid was filtered through a celite bed
  5. washwashed with EtOAc (150 mL)
  6. customThe EtOAc layer was separated from the filtrate solution
  7. washwashed with water (2×100 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b943a218c56d48dc861cd550476831fc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732613B2

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