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Hydrochloric Acid → 4-Amino-3,6-dihydroxy-1-naphthalenesulfonic acid

HRID 1613117
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1613117
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[N:13]=O.[S:15]([O-:18])([OH:17])=[O:16].[Na+].S(=O)(O)[O-].Cl>O>[OH:1][C:2]1[CH:11]=[C:10]([S:15]([OH:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[NH2:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 104748BisulfiteHCID 13750455HCID 13750455, VerbindungHCID 23665763Sodium Bisulfite

Produkt 1

HCID 150551094-Amino-3,6-dihydroxy-1-naphthalenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

In the second reaction stage, the 2,7-dihydroxy-1-nitrosonaphthalene (I) which is generally still moist with water and which reacts in the tautomeric oxime form (Ia), is first suspended, according to Boninger, Chem. Ber. 27, 3050 (1894), in commercially-available 37% aqueous sodium hydrogen sulfite solution and stirred at about 20°-25° C. until it is completely dissolved. The bisulfite addition compound (IIa) thus formed is not isolated, but the brown reaction solution is acidified with hydrochloric acid and heated to about 25°-60° C. 2,7-Dihydroxy-1-aminonaphthalene-4-sulfonic acid (II) is formed by reduction of the nitroso group and aromatization of the cycloaliphatic ring system. The aminonaphtholsulfonic acid (II) is isolated by filtering off the resulting light-gray crystals with suction, washing these on a suction filter first with water and then with methanol and, if desired, drying them. The reaction product thus prepared is used without further purification, if appropriate still moist, for the next reaction stage. The yield of reaction product II is about 90-95% of theory. ##STR6##

Aufarbeitung

  1. customIn the second reaction stage
  2. dissolutionis completely dissolved
  3. customthus formed
  4. customis not isolated
  5. temperatureheated to about 25°-60° C

Quellen und Nachweise

ORD-Eintrag
ord-ec1c22300f1a438599e3759fa930f390
Quelldatensatz
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05192640

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