N-hydroxy-4-nitrobenzamide synthesis
- Product Name:N-hydroxy-4-nitrobenzamide
- CAS Number:1613-76-9
- Molecular formula:C7H6N2O4
- Molecular Weight:182.13
62-23-7
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Yield:1613-76-9 70%
Reaction Conditions:
with hydroxylamine hydrochloride;1,1'-carbonyldiimidazole in N,N-dimethyl-formamide; for 20 h;
Steps:
Method a
General procedure: Acid (4 mmol) was dissolved in DMF (2 mL), and CDI (0.65 g, 4 mmol) in DMF (2 mL) was slowly added. After 2 h hydroxylamine hydrochloride (0.56 g, 8 mmol; as well as 0.67 g, 8 mmol of N- or O-methylated hydroxylamine hydrochloride) was added in one portion and mixture was shortly stirred until salt disappearance and incubated for additional 18 hours. The solution was poured into water, extracted with ethyl acetate and dried over Na2SO4. The solvent was removed at reduced pressure, and the oil was chromatographed on SiO2, eluting with CHCl3/EtOH, to give the raw product that was finally purified by washing with appropriate organic solvents. Yields 30-70 %.
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
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