N,2-dihydroxy-5-nitrobenzaMide synthesis

Yield:61494-42-6 30%

Reaction Conditions:

with hydroxylamine hydrochloride;triethylamine in water;dimethyl sulfoxide at 50; for 3 h;

Steps:

Method b

General procedure: Methyl 5-nitrosalicylate (0.79 g, 4 mmol) in DMSO (8 ml) and hydroxylamine hydrochloride (0.60 g, 8,6 mmol) in H₂O (2 ml) were mixed followed by addition of triethylamine (0.80 g, 8 mmol) and mixture was incubated for 3 h at 50 °C. The solution was cooled and poured into water (30 ml) and unreacted ester was removed by filtration. Filtrate was extracted by ethylacetate (50 ml), organic phase was washed with water (40 ml) and brine (40 ml) and dried over Na₂SO₄. The solvent was removed at reduced pressure, and the raw product that was finally purified by washing with MeCN (3 ml). Yield 30 %.

References:

Kozlov, Maxim V.;Kleymenova, Alla A.;Romanova, Lyudmila I.;Konduktorov, Konstantin A.;Smirnova, Olga A.;Prasolov, Vladimir S.;Kochetkov, Sergey N. [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 21,p. 5936 - 5940] Location in patent:supporting information