ChemicalBook CAS DataBase List 3-METHOXY-5-NITROANILINE

3-METHOXY-5-NITROANILINE synthesis

7synthesis methods

Product Name:3-METHOXY-5-NITROANILINE
CAS Number:586-10-7
Molecular formula:C7H8N2O3
Molecular Weight:168.15

5327-44-6 Synthesis

5327-44-6
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586-10-7
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Yield: 93%

Reaction Conditions:

with sodium sulfide;sodium hydrogencarbonate in methanol;water for 0.5 h;Heating / reflux;

Steps:

12.1
Example 124-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy}-butyric acid Step 1: Preparation of 3-methoxy-5-nitro-phenylamine; Sodium bicarbonate (5.62 g, 66.87 mmol) was added to a solution of sodium sulfide (5.5 g, 70.58 mmol) in deionized water (60 mL). When the sodium bicarbonate was completely dissolved, methanol (50 mL) was added, and the solution was cooled to 0° C. A precipitate formed, which was removed by filtration through a Celite pad. The filtered solution was added quickly to a solution of 3,5-dinitroanisole (7.36 g, 37.15 mmol) in methanol (50 mL). The resulting suspension was heated to reflux for 30 min and then the solution was concentrated in vacuo to remove methanol. The aqueous residue was poured into 200 mL of ice-water, and the resulting orange precipitate was collected by filtration. After air-drying, 3-methoxy-5-nitro-phenylamine (5.82 g, 93%) was obtained as light brown solid: ES(+)-HRMS m/e calculated for C₇H₈N₂O₃(M+H)⁺ 169.0608, found 169.0608.

References:

Dominique, Romyr;Fotouhi, Nader;Gillespie, Paul;Goodnow, Robert Alan;Kowalczyk, Agnieszka;Qiao, Qi;Sidduri, Achyutharao US2009/54466, 2009, A1 Location in patent:Page/Page column 29