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 W Macomber, Terrance P. Smith

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 languageEnglish (US)
Pages (from-to)405-417
Number of pages13
JournalSynthetic Communications
Volume23
Issue number3
DOIs
StatePublished - Feb 1 1993

Fingerprint

Ether
Amines
Chlorides
Hydrolysis
Derivatives
Acids
2-naphthol
alizarin violet
2-nitroanisole
benzenesulfonamide

Cite this

A Novel Method for the Preparation of 3-Amino-4-Hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives. / Katritzky, Alan R.; Wu, Jing; Rachwal, Stanislaw; Macomber, David W; Smith, Terrance P.

In: Synthetic Communications, Vol. 23, No. 3, 01.02.1993, p. 405-417.

Research output: Contribution to journalArticle

Katritzky, Alan R. ; Wu, Jing ; Rachwal, Stanislaw ; Macomber, David W ; Smith, Terrance P. / A Novel Method for the Preparation of 3-Amino-4-Hydroxybenzenesulfonamide Precursors of “Acid Alizarin Violet N” Derivatives. In: Synthetic Communications. 1993 ; Vol. 23, No. 3. pp. 405-417.
@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 Macomber, {David W} and Smith, {Terrance P.}",
year = "1993",
month = "2",
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 W

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 - http://www.scopus.com/inward/record.url?scp=0027457564&partnerID=8YFLogxK

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

U2 - 10.1080/00397919308009795

DO - 10.1080/00397919308009795

M3 - Article

VL - 23

SP - 405

EP - 417

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 3

ER -