Hydroxylamine → Nodan

HRID 868386

Reaktionsgleichung

Reaktionsgleichung von HRID 868386
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].[CH:15]1C2C(=CC=CC=2)C=C[C:16]=1[OH:25].[NH2:26]O.C(OC(=O)C)(=O)C>C(O)(=O)C>[C:16]([NH:26][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:14]=[CH:13]2)(=[O:25])[CH3:15]

Komponenten

6

Edukt 4

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 86632-NaphtholHCID 737092-Naphthyl acetate

Produkt 1

HCID 14273985Nodan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

In accordance with this invention, N,O-diacetyl-6-amino-2-naphthol (NODAN) is produced from 2-naphthyl acetate, or 2-naphthol and an acetylating agent such as acetic acid or anhydride, by means of an integrated process including the steps of converting the 2-naphthyl acetate, or 2-naphthol and acetylating agent, to 6-hydroxy-2-acetonaphthone (6,2-HAN) by a Fries rearrangement or Friedel-Crafts acetylation respectively, and converting the 6,2-HAN or its acetate esters, i.e., 6-acetoxy-2-acetonaphthone (6,2-AAN) to 6,2-HAN oxime with a hydroxylamine salt. The oxime is then subjected to a Beckmann rearrangement and accompanying acetylation by contacting the oxime with acetic anhydride and a Beckmann rearrangement catalyst to form NODAN.

Quellen und Nachweise

ORD-Eintrag
ord-bfa46a75e1a44520b2f83f3b4157710f
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04778922

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