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

HRID 445436

Reaktionsgleichung

Reaktionsgleichung von HRID 445436
C([O-])(=O)C.[NH4+].[CH2:6]([O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22](=[O:24])[CH3:23])=[C:16]([N+:25]([O-])=O)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>[Fe].O>[NH2:25][C:16]1[CH:15]=[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:19]([O:20][CH3:21])=[CH:18][C:17]=1[C:22](=[O:24])[CH3:23]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

Produkt 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A Mixture of iron powder (477 mmol, 27 g), ammonium acetate (500 mmol, 31.g), 1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-ethanone (120 mmol, 36 g), toluene (500 ml) and water (500 ml) was refluxed overnight, or until completion. The mixture was filtered through celite and washed with EtOAc. The organic layer washed with water and Sat. NaCl, dried over Na2SO4, and concentrated to afford the product, 90%. 1H NMR (CDCl3): 7.408-7.298 (5H, m), 7.130 (1H, s), 6.155 (2H, br), 6.104 (1H, s), 5.134 (2H, s), 3.834 (3H, s), 2.507 (3H, s). LC/MS (M+1=272).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered through celite
  3. washwashed with EtOAc
  4. washThe organic layer washed with water and Sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the product, 90%

Quellen und Nachweise

ORD-Eintrag
ord-2ec2c040a76a4d408a6f9f4a6bfe50cb
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476298B2

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