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

Alan R. Katritzky; Jing Wu; Stanislaw Rachwal; David Macomber; Terrance P. Smith

doi:10.1080/00397919308009795

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

Alan R. Katritzky, Jing Wu, Stanislaw Rachwal, David Macomber, Terrance P. Smith

Medicine - General Internal Medicine

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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- l-naphthyl)azobenzenesulfonamide (1d).

Original language	English (US)
Pages (from-to)	405-417
Number of pages	13
Journal	Synthetic Communications
Volume	23
Issue number	3
DOIs	https://doi.org/10.1080/00397919308009795
State	Published - Feb 1 1993

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title = "A Novel Method for the Preparation of 3-Amino-4-Hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives",

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- l-naphthyl)azobenzenesulfonamide (1d).",

author = "Katritzky, {Alan R.} and Jing Wu and Stanislaw Rachwal and David Macomber and Smith, {Terrance P.}",

year = "1993",

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T1 - A Novel Method for the Preparation of 3-Amino-4-Hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives

AU - Katritzky, Alan R.

AU - Wu, Jing

AU - Rachwal, Stanislaw

AU - Macomber, David

AU - Smith, Terrance P.

PY - 1993/2/1

Y1 - 1993/2/1

N2 - 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- l-naphthyl)azobenzenesulfonamide (1d).

AB - 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- l-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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