Ammonium Chloride → 4-(Pyridin-3-Yloxy)Aniline

HRID 336437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336437
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH:2]=1.[Cl-].[NH4+]>O.O1CCCC1.CO.[Fe]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:2]=1

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 1199023-(4-Nitrophenoxy)pyridine

Produkt 1

HCID 31596314-(Pyridin-3-Yloxy)AnilineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(Pyridin-3-yl)oxy-1-nitrobenzene prepared in Step A was dissolved in the mixture of water (100 mL), tetrahydrofuran (100 mL) and methanol (100 mL). Iron powder (103 g, 1.84 mol) and ammonium chloride (99 g, 1.84 mol) were added thereto, and the mixture was stirred for 3 h at 80° C. using a mechanical stirrer. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with methanol, and concentrated under reduced pressure. The solid thus obtained was filtered, washed with ether, and dried to give the title compound (17 g, Yield 36%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through a cellite
  3. washwashed with methanol
  4. concentrationconcentrated under reduced pressure
  5. customThe solid thus obtained
  6. filtrationwas filtered
  7. washwashed with ether
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f2cf162be07445fc8c94bb6e87175ec1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889691B2

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