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

Publisher link

10.1080/00397919308009795

Find It

Find It at U of M Libraries

Cite this

@article{4fcbcd2e5373488cbe12acf7a7d2c866,

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",

month = feb,

day = "1",

doi = "10.1080/00397919308009795",

language = "English (US)",

volume = "23",

pages = "405--417",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "3",

}

TY - JOUR

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).

UR - https://www.scopus.com/pages/publications/0027457564

UR - https://www.scopus.com/inward/citedby.url?scp=0027457564&partnerID=8YFLogxK

U2 - 10.1080/00397919308009795

DO - 10.1080/00397919308009795

M3 - Article

AN - SCOPUS:0027457564

SN - 0039-7911

VL - 23

SP - 405

EP - 417

JO - Synthetic Communications

JF - Synthetic Communications

IS - 3

ER -

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

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this