N-(3,6-Dimethoxy-2-nitrophenyl)acetamide

Lina A. Al-Dulaimi; Joseph C. Bear; Jeremy K. Cockcroft; Giuseppe Trigiante; Fawaz Aldabbagh

doi:10.3390/M2147

N-(3,6-Dimethoxy-2-nitrophenyl)acetamide

University College London

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

Abstract

1,4-Dimethoxy-2,3-dinitrobenzene (1) reduction using sodium hydrosulfite resulted in 3,6-dimethoxybenzene-1,2-diamine (2) and 3,6-dimethoxy-2-nitroaniline (3) in 24% and 59% yields, respectively. Nitroaniline 3 was acetylated with acetyl chloride to give N-(3,6-dimethoxy-2-nitrophenyl)acetamide (4) in a 65% yield and with acetic anhydride to give N-acetyl-N-(3,6-dimethoxy-2-nitrophenyl)acetamide (5) in 78% yield. Novel compounds 4 and 5 were characterized by FT-IR, ¹H and ¹³C-NMR, and HRMS. The X-ray crystal structure of acetamide 4 is also presented.

Original language	English
Article number	M2147
Journal	MolBank
Volume	2026
Issue number	2
Early online date	10 Mar 2026
DOIs	https://doi.org/10.3390/M2147
Publication status	Published - Apr 2026

Keywords

aniline
benzoquinone
nitrobenzene
reduction
sodium dithionite

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10.3390/M2147Licence: CC BY

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title = "N-(3,6-Dimethoxy-2-nitrophenyl)acetamide",

abstract = "1,4-Dimethoxy-2,3-dinitrobenzene (1) reduction using sodium hydrosulfite resulted in 3,6-dimethoxybenzene-1,2-diamine (2) and 3,6-dimethoxy-2-nitroaniline (3) in 24\% and 59\% yields, respectively. Nitroaniline 3 was acetylated with acetyl chloride to give N-(3,6-dimethoxy-2-nitrophenyl)acetamide (4) in a 65\% yield and with acetic anhydride to give N-acetyl-N-(3,6-dimethoxy-2-nitrophenyl)acetamide (5) in 78\% yield. Novel compounds 4 and 5 were characterized by FT-IR, 1H and 13C-NMR, and HRMS. The X-ray crystal structure of acetamide 4 is also presented.",

keywords = "aniline, benzoquinone, nitrobenzene, reduction, sodium dithionite",

author = "Al-Dulaimi, \{Lina A.\} and Bear, \{Joseph C.\} and Cockcroft, \{Jeremy K.\} and Giuseppe Trigiante and Fawaz Aldabbagh",

year = "2026",

month = apr,

doi = "10.3390/M2147",

language = "English",

volume = "2026",

journal = "MolBank",

issn = "1422-8599",

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TY - JOUR

T1 - N-(3,6-Dimethoxy-2-nitrophenyl)acetamide

AU - Al-Dulaimi, Lina A.

AU - Bear, Joseph C.

AU - Cockcroft, Jeremy K.

AU - Trigiante, Giuseppe

AU - Aldabbagh, Fawaz

PY - 2026/4

Y1 - 2026/4

N2 - 1,4-Dimethoxy-2,3-dinitrobenzene (1) reduction using sodium hydrosulfite resulted in 3,6-dimethoxybenzene-1,2-diamine (2) and 3,6-dimethoxy-2-nitroaniline (3) in 24% and 59% yields, respectively. Nitroaniline 3 was acetylated with acetyl chloride to give N-(3,6-dimethoxy-2-nitrophenyl)acetamide (4) in a 65% yield and with acetic anhydride to give N-acetyl-N-(3,6-dimethoxy-2-nitrophenyl)acetamide (5) in 78% yield. Novel compounds 4 and 5 were characterized by FT-IR, 1H and 13C-NMR, and HRMS. The X-ray crystal structure of acetamide 4 is also presented.

AB - 1,4-Dimethoxy-2,3-dinitrobenzene (1) reduction using sodium hydrosulfite resulted in 3,6-dimethoxybenzene-1,2-diamine (2) and 3,6-dimethoxy-2-nitroaniline (3) in 24% and 59% yields, respectively. Nitroaniline 3 was acetylated with acetyl chloride to give N-(3,6-dimethoxy-2-nitrophenyl)acetamide (4) in a 65% yield and with acetic anhydride to give N-acetyl-N-(3,6-dimethoxy-2-nitrophenyl)acetamide (5) in 78% yield. Novel compounds 4 and 5 were characterized by FT-IR, 1H and 13C-NMR, and HRMS. The X-ray crystal structure of acetamide 4 is also presented.

KW - aniline

KW - benzoquinone

KW - nitrobenzene

KW - reduction

KW - sodium dithionite

U2 - 10.3390/M2147

DO - 10.3390/M2147

M3 - Article

AN - SCOPUS:105037554629

SN - 1422-8599

VL - 2026

JO - MolBank

JF - MolBank

IS - 2

M1 - M2147

ER -

N-(3,6-Dimethoxy-2-nitrophenyl)acetamide

Abstract

Keywords

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