1-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one → 1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

HRID 470984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470984
[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]=1

Komponenten

4

Edukt 1

HCID 579889911-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one

Produkt 1

HCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Zinc dust (5.5 g) was added portionwise to a suspension of 1-(4-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone (example 11, step b) (5.5 g) in acetic acid (55 mL) over 15 minutes, whilst maintaining the internal temperature below 40° C. with an ice bath. The mixture was allowed to attain ambient temperature and stirred for 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. Yield 4.8 g.

Aufarbeitung

  1. temperaturewhilst maintaining the internal temperature below 40° C. with an ice bath
  2. customto attain ambient temperature
  3. filtrationThe mixture was filtered through Celite (Caution
  4. customto dry),
  5. washwashed with acetic acid
  6. additionthe filtrate poured onto ice/water (500 mL)
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with water
  9. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-6af414e5f1ef4919b8b88588f18d2c0b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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