4-Aminophenol → 4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

HRID 503525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503525
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:16]1[CH:17]=[CH:18][N:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([O:26][CH3:27])=[CH:21]2>CN(C=O)C>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:17][CH:18]=[N:19]2)=[N:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Produkt 1

HCID 441851064-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Alternatively, the title compound may be prepared by the following method: In a nitrogen purged sealed pressure vessel, dissolved 4-aminophenol (0.617 g, 5.65 mmol) in DMF (0.030 L). Cesium carbonate (3.68 g, 11.3 mmol) was added and the mixture was stirred at RT for 5 min. Added 8-chloro-3-methoxy-1,5-naphthyridine (1.00 g, 5.14 mmol), heated to 90° C., stirred for 17 h. The mixture was allowed to cool to RT and was concentrated. The crude material was triturated with methanol, filtered, washed with methanol followed by water, and air dried to yield 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as brown solid. MS [M+H]=268.1; Calc'd 267.3 for C15H13N3O2.

Aufarbeitung

  1. customIn a nitrogen purged
  2. customsealed pressure vessel
  3. stirringstirred for 17 h
  4. temperatureto cool to RT
  5. concentrationwas concentrated
  6. customThe crude material was triturated with methanol
  7. filtrationfiltered
  8. washwashed with methanol
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b69e8e292db245689cbde846064e00b7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776857B2

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