ChemicalBook CAS DataBase List 1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE

1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE synthesis

5synthesis methods

Product Name:1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE
CAS Number:4101-32-0
Molecular formula:C10H11NO5
Molecular Weight:225.2

1131-62-0

4101-32-0

General procedure for the synthesis of 1-(4,5-dimethoxy-2-nitrophenyl)ethanone from 3,4-dimethoxyacetophenone: (1) Nitration step: a solution was prepared by dissolving 3,4-dimethoxyacetophenone (1,500 g) in 17% nitric acid (1,400 g) at 5 to 10 °C, followed by slow dropwise addition to a solution consisting of 67% nitric acid (8430 g) and sodium nitrite (18 g) (18 g). The titration process was controlled to be completed within 2 to 3 hours. After the dropwise addition, the reaction solution was continued to be stirred at 5 to 10°C for 1 to 2 hours. Cold water (7.5 L) was added to dilute the reaction mixture and stirred for 30 minutes. The reaction mixture was filtered and the filter cake was washed with water (30 L). The solid product obtained by filtration was re-suspended in water (7.5 L), neutralized with aqueous sodium bicarbonate to pH neutral, filtered again and washed with water (7 L). Finally, the product was dried under reduced pressure to afford 3,4-dimethoxy-6-nitroacetophenone (2164 g, 87.9% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3): δ 2.50 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 6.76 (s, 1H), 7.62 (s, 1H).

1131-62-0
327 suppliers
$14.00/5g

4101-32-0
114 suppliers
$22.39/1G

Yield: 89.4%

Reaction Conditions:

with nitric acid in dichloromethane at -10; for 2 h;

Steps:

1.2. General procedure for preparation of(1)
A mixture of 3,4-dimethoxyacetophenone (100.0 g, 0.6 mol) in CH₂Cl₂(500 mL, 5 v/w) was stirred at -10^oC.98% HNO₃(70 mL) was added slowly dropwise and then was stirred for 2 h. The reaction solution was poured into ice water with vigorous stirring, and the aqueous phase was extracted with dichloromethane, washed with water, dried over Na₂SO₄and then concentrated under reduced pressure to give compound1as a yellow solid in 89.4% yield.

References:

Xu, Qiaoling;Dai, Baozhu;Li, Zhiwei;Xu, Le;Yang, Di;Gong, Ping;Hou, Yunlei;Liu, Yajing [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 19,art. no. 126630] Location in patent:supporting information