A Novel Method for the Preparation of 3-Amino-4-hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives

Alan R. Katritzky Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-2046

Jing Wu Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-2046

Stanislaw Rachwal Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-2046

David Macomber 3M Company, Graphics Sector Laboratory 3M Center, Hudson Road, St. Paul, MN 55144-1000

Terrance P. Smith Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-2046

Abstract

Chlorosulfonation of 2-nitroanisole gave 4-methoxy-3-nitrobenzenesulfonyl chloride (7) which was converted with N-butyl(3-phenylpropyl) amine into benzenesulfonamide (8). Hydrolysis of the ether and reduction of the nitro group of 8 followed by diazotization and coupling with 2-naphthol gave N-Butyl-N-(3-phenylpropyl)-4-hydroxy-3-(2-hydroxy-1-naphthyl) azobenzenesulfonamide (1d).

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A Novel Method for the Preparation of 3-Amino-4-hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives

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A Novel Method for the Preparation of 3-Amino-4-hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives

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