1-Naphthylamine → Hydrazine, 1-naphthalenyl-

HRID 1870957

Reaktionsgleichung

Reaktionsgleichung von HRID 1870957
[N:1]([O-])=O.[Na+].[C:5]1([NH2:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O.Cl>[C:5]1([NH:15][NH2:1])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 86401-NaphthylamineHCID 23668193Sodium Nitrite

Produkt 1

HCID 75240Hydrazine, 1-naphthalenyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium nitrite (4.8 g) in water (20 ml) was added over 15 minutes to a stirred ice-cold suspension of 1-naphthylamine (9.58 g) in 6 M hydrochloric acid (80 ml). After an additional 30 minutes in the ice bath,, stannous chloride (44.5 g) in 6 M hydrochloric acid (80 ml) was added slowly and the resulting suspension was stirred at 0° for 3 hr. The resulting solid was filtered off and dissolved in a mixture of 40% potassium hydroxide solution (100 ml) and ethyl acetate (150 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried and concentrated under reduced pressure to afford the title compound as a purple solid (10.58 g Rf =0.1 in EA/CH (1/4)). I.R. (cm-1):3312-3474(NH and NH2); 1580-1610,(C=C)

Aufarbeitung

  1. filtrationThe resulting solid was filtered off
  2. dissolutiondissolved in a mixture of 40% potassium hydroxide solution (100 ml) and ethyl acetate (150 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×100 ml)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated under reduced pressure
  7. customto afford the title compound as a purple solid (10.58 g Rf =0.1 in EA/CH (1/4))

Quellen und Nachweise

ORD-Eintrag
ord-2689de7f705d42a08418eb334cd02989
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100289

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