4-Methoxy-1-naphthol → HCID 178493282, Verbindung

HRID 46416

Reaktionsgleichung

Reaktionsgleichung von HRID 46416
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.[N:11]([O-])=O.[Na+].[CH3:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:27])=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>Cl.O.[OH-].[Na+]>[NH:6]1[C:5]2[CH:9]=[CH:10][C:2]([N:1]=[N:11][C:19]3[CH:18]=[C:17]([O:16][CH3:15])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]=3[OH:27])=[CH:3][C:4]=2[N:8]=[N:7]1

Komponenten

8

Edukt 4

HCID 665424-Methoxy-1-naphtholHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178507366HCID 178507366, Verbindung

Produkt 1

HCID 178493282HCID 178493282, VerbindungAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Aminobenzotriazole (4.3 g) was dissolved in a mixture of concentrated hydrochloric acid (24 ml) and water (100 ml) and diazotized at 0° C. with a solution of sodium nitrite (2.2 g) in water (15 ml). The resulting diazonium solution was added at 0° C. to 4-methoxynaphth-1-ol (5.3 g) dissolved in 3 N sodium hydroxide (90 ml) containing sodium acetate (20 g). The resulting mixture was stirred for one hour at 0° C. and then acidified with hydrochloric acid. The dye was filtered off and crystallized in a pyridine/water mixture to give pure material (7.4 g), m.p. 254° C., λmax (methanol)=516 nm.

Aufarbeitung

  1. filtrationThe dye was filtered off
  2. customcrystallized in a pyridine/water mixture

Quellen und Nachweise

ORD-Eintrag
ord-df0b56c0082845c8b6524ba117efcee5
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173478

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