Improved Synthesis of 3-Nitrosalicylic Acid

REFERENCES

• (a) Merritt , J. R. ; Rokosz , L. L. ; Nelson , K. H. ; Kaiser , B. ; Wang , W. ; Stauffer , T. M. ; Ozgur , L. E. ; Schilling , A. ; Li , G. ; Baldwin , J. J. ; Taveras , A. G. ; Dwyer , M. P. ; Chao , J. Synthesis and structure–activity relationships of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists. Bioorg. Med. Chem. Lett. 2006, 16, 4107–4110; (b) Usuki , Y. ; Adachi , N. ; Fujita , K.-I. ; Ichimura , A. ; Iio , H. ; Taniguchi , M. Structure–activity relationship studies on UK-2A, a novel antifungal antibiotic from Streptomyces sp. 517-02, Part 5: Roles of the nine-membered dilactone-ring moiety in respiratory inhibition. Bioorg. Med. Chem. Lett. 2006, 16, 3319–3322; (c) Dickie , J. P. ; Loomans , M. E. ; Farley , T. M. ; Strong , F. M. The chemistry of antimycin A, XI: N-Substituted 3-formamidosalicylic amides. J. Med. Chem. 1963, 6, 424–427; (d) Dwyer , M. P. ; Yu , Y. ; Chao , J. ; Aki , C. ; Chao , J. ; Biju , P. ; Girijavallabhan , V. ; Rindgen , D. ; Bond , R. ; Mayer-Ezel , R. ; Jakway , J. ; Hipkin , R. W. ; Fossetta , J. ; Gonsiorek , W. ; Bian , H. ; Fan , X. ; Terminelli , C. ; Fine , J. ; Lundell , D. ; Merritt , J. R. ; Rokosz , L. L. ; Kaiser , B. ; Li , G. ; Wang , W. ; Stauffer , T. ; Ozgur , L. ; Baldwin , J. ; Taveras , A. G. Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enyl-amino}benzamide (SCH 527123): A potent, orally bioavailable CXCR2/CXCR1 receptor antagonist. J. Med. Chem. 2006, 49, 7603–7606; (e) Wu , M. T. ; Lyle , R. E. Synthesis of some simple antimycin analogs. J. Heterocycl. Chem. 1971, 8, 989–991.
   PubMed Web of Science ®Google Scholar
• Meldrum , A. N. ; Hirve , N. W. Derivatives of salicylic acid, Part I: 3-Nitro- and 5-nitrosalicylic acids . J. Ind. Chem. Soc. 1928 , 5 , 95 – 101 .
   Google Scholar
• (a) Andreozzi , R. ; Canterino , M. ; Caprio , V. ; Di Somma , I. ; Sanchirico , R. Solubility of 5-nitro- and 3-nitrosalicylic acids in an acetic acid/nitric acid mixture . J. Chem. Eng. Data 2007 , 52 , 122 – 125 ; (b) Andreozzi , R. ; Canterino , M. ; Caprio , V. ; Di Somma , I. ; Sanchirico , R. Batch salicylic acid nitration by nitric acid/acetic acid mixture under isothermal, isoperibolic, and adiabatic conditions . J. Hazard. Mater. 2006 , A138 , 452 – 458 ; (c) Andreozzi , R. ; Caprio , V. ; Di Somma , I. ; Sanchirico , R. Kinetic and safety assessment for salicylic acid nitration by nitric acid/acetic system . J. Hazard. Mater. 2006 , A134 , 1 – 7 ; (d) Andreozzi , R. ; Canterino , M. ; Caprio , V. ; Di Somma , I. ; Sanchirico , R. Salicylic acid nitration by means of nitric acid/acetic acid system: Chemical and kinetic characterization . Org. Proc. Res. Dev. 2006 , 10 , 1199 – 1204 .
   Google Scholar
• Deninger , A. Nitrirung der Oxybenzoesäuren durch salpetrige Säure . J. Prakt. Chem. 1890 , 42 , 550 – 553 .
   Google Scholar
• Iranpoor , N. ; Firouzabadi , H. ; Heydari , R. ; Shiri , M. Nitration of aromatic compounds by Zn(NO3)2·2N2O4 and its charcoal-supported system . Synth. Commun. 2005 , 35 , 263 – 270 .
   Web of Science ®Google Scholar
• Chawla , H. M. ; Mittal , R. S. Decarboxylative nitration of some simple hydroxybenzoic acids using cerium(IV) ammonium nitrate . Ind. J. Chem. 1983 , 22B , 1129 – 1131 .
   Google Scholar
• Ganguly , N. C. ; Dutta , S. ; Datta , M. ; De , P. Solid-state regioselective nitration of activated hydroxyaromatics and hydroxycoumarins with cerium(IV) ammonium nitrate . J. Chem. Res. 2005 , 733 – 735 .
   Google Scholar
• Learmonth , D. A. Nitration of phenolic compounds . Brit. Patent GB 2377934, 2003; WO Patent 2003011810 .
   Google Scholar
• Brochet , C. Monopropellant detonation: Isopropyl nitrate . Astronautica Acta 1970 , 15 , 419 – 425 .
   Google Scholar