Hydroxylamine → Nodan

Participants

Reaction Steps

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.

Provenance & Evidence