3,6-Dimethoxy-2-nitroaniline synthesis

9synthesis methods

Product Name:3,6-Dimethoxy-2-nitroaniline
CAS Number:26002-57-3
Molecular formula:C8H10N2O4
Molecular Weight:198.18

6945-76-2
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26002-57-3
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Yield:26002-57-3 95%

Reaction Conditions:

Stage #1: 2,3-dinitro-1,4-dimethoxybenzenewith iron(III) trichloride hexahydrate in methanol at 65; for 1 h;
Stage #2: with hydrazine hydrate monohydrate in methanol at 65; for 1 h;

Steps:

4.1.5. Synthesis of 3,6-dimethoxy-2-nitroaniline (6)

A mixture of 1,4-dimethoxy-2,3-dinitrobenzene (4.56 g, 20 mmol) (1), activated charcoal (0.8 g), iron (III) chloride hexahydrate (324.4 mg, 1.2 mmol) in methanol (25 mL), was stirred at 65°C for 1 h. Then, hydrazine monohydrate (3.84 mL, 79 mmol) was added drop wise and stirred at 65°C for 1 h. The reaction was allowed to cool to room temperature and the solids were filtered and washed with methanol. The filtrate was dried (MgSO₄), concentrated and the residue was purified by column chromatography (ethyl acetate/hexane, 1:1) to give 6 as an orange solid (3.76 g, 95%), mp 68-69°C (lit. [28] 67-68°C).

References:

López-Lira, Claudia;Tapia, Ricardo A.;Herrera, Alejandra;Lapier, Michel;Maya, Juan D.;Soto-Delgado, Jorge;Oliver, Allen G.;Graham Lappin;Uriarte, Eugenio [Bioorganic Chemistry,2021,vol. 111,art. no. 104823]

150-78-7 Synthesis