1-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one → 1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone
Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:19][C:10]1[C:11]([OH:18])=[C:12]([C:15](=[O:17])[CH3:16])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Zinc dust (5.5 g) was added portionwise to a suspension of 1-(4-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone (5.5 g) in acetic acid (55 mL) over 15 min, whilst maintaining the internal temperature below 40° C. with an ice bath. The mixture was allowed to attain ambient temperature and stirred for a further 2 h. The mixture was filtered through Celite (caution gets hot, do not allow to dry), washed with acetic acid, and the filtrate poured onto ice/water (500 mL). The resulting precipitate was filtered off, washed with water, and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid (4.8 g). 1H NMR (300 MHz, DMSO-d6) δ 7.53 (m, 2H), 7.48-7.33 (m, 3H), 7.28 (d, J=9.0 Hz, 1H), 6.72 (d, J=9.0 Hz, 1H), 5.29 (s, 2H), 2.59 (s, 3H).
Aufarbeitung
- temperaturewhilst maintaining the internal temperature below 40° C. with an ice bath
- customto attain ambient temperature
- filtrationThe mixture was filtered through Celite (caution
- customto dry),
- washwashed with acetic acid
- additionthe filtrate poured onto ice/water (500 mL)
- filtrationThe resulting precipitate was filtered off
- washwashed with water
- customdried under vacuum at 40° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-a922e1c2bb5d47f1adccbf721ff18f8e
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08017602B2
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