Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid

Younis Baqi, Christa E. Müller

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

(Chemical Equation Presented) The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic and aromatic amines 2a-w without added solvent or catalyst. Up to >99% isolated yield was obtained within 5-30 min at 80-120°C. The reaction, which is suitable for upscaling, yielded new compounds that are of considerable interest as useful building blocks and as potential drugs.

Original languageEnglish
Pages (from-to)5908-5911
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number15
DOIs
Publication statusPublished - Jul 20 2007

Fingerprint

Amination
Amines
Microwaves
Derivatives
Catalysts
Acids
Pharmaceutical Preparations
2-chloro-5-nitrobenzoic acid
2-chlorobenzoic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid. / Baqi, Younis; Müller, Christa E.

In: Journal of Organic Chemistry, Vol. 72, No. 15, 20.07.2007, p. 5908-5911.

Research output: Contribution to journalArticle

@article{93931b8d19404f79b75cc6bf8baabc92,
title = "Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid",
abstract = "(Chemical Equation Presented) The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic and aromatic amines 2a-w without added solvent or catalyst. Up to >99{\%} isolated yield was obtained within 5-30 min at 80-120°C. The reaction, which is suitable for upscaling, yielded new compounds that are of considerable interest as useful building blocks and as potential drugs.",
author = "Younis Baqi and M{\"u}ller, {Christa E.}",
year = "2007",
month = "7",
day = "20",
doi = "10.1021/jo070731i",
language = "English",
volume = "72",
pages = "5908--5911",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "15",

}

TY - JOUR

T1 - Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid

AU - Baqi, Younis

AU - Müller, Christa E.

PY - 2007/7/20

Y1 - 2007/7/20

N2 - (Chemical Equation Presented) The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic and aromatic amines 2a-w without added solvent or catalyst. Up to >99% isolated yield was obtained within 5-30 min at 80-120°C. The reaction, which is suitable for upscaling, yielded new compounds that are of considerable interest as useful building blocks and as potential drugs.

AB - (Chemical Equation Presented) The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic and aromatic amines 2a-w without added solvent or catalyst. Up to >99% isolated yield was obtained within 5-30 min at 80-120°C. The reaction, which is suitable for upscaling, yielded new compounds that are of considerable interest as useful building blocks and as potential drugs.

UR - http://www.scopus.com/inward/record.url?scp=34547125958&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547125958&partnerID=8YFLogxK

U2 - 10.1021/jo070731i

DO - 10.1021/jo070731i

M3 - Article

VL - 72

SP - 5908

EP - 5911

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -