zinc acetic acid reduction of nitro

In fact in both articles they reduce 4-nitro-cinnamic acid to the 4-amino counterpart in very good (90%) yield, no double bond getting reduced. DOI: 10.1021/jo50014a011. Molecular Weight: 125.4 g/mol. 0000004487 00000 n 659). Learn more. Room-temperature ionic liquids. Google Scholar. Acetic acid solution: Glacial acetic acid was diluted in water to provide 20 % (v/v) solution. The reaction can also be effected through radical reaction with tributyltin hydride and a radical initiator, AIBN as an example.[17]. (Zn) [7440‐66‐6] Zn (MW 65.39) Synthesis, 1974, 726–727. Tetrahedron Letters, 25, 839–842. The conversion can be effected by many reagents. Part XVI. DOI: 10.1016/j.tetlet.2005.06.126. Sarmah, P., & Dutta, D. K. (2003). Ram, S., & Ehernkaufer, R. E. (1984). Water is the proton source. DOI:10.1016/s0040-4039(01)91034-2. Encyclopedia of Reagents for Organic Synthesis. Johnstone, R. A. W., Willby, A. H., & Entwistle, I. D. (1985). The reaction can also be effected through radical reaction with tributyltin hydride and a radical initiator, AIBN as an example. A mild, environmentally friendly method for reduction of aromatic nitro group to amine is reported, using zinc powder in aqueous solutions of chelating ethers. O’Neil, M. J. Browse other articles of this reference work: The full text of this article hosted at iucr.org is unavailable due to technical difficulties. The latter compound was reduced with zinc in acetic acid to 3β-acetylamino-5α-cholestan-2-one ( 8 ). Each mL of nitrite sample was added one scoopful (454 ± 10 mg) of diazotiza-tion powder followed by 9 mL of acetic acid solution. ���>��_N��K.���֓a�p�j�?ޝ��s@E���ƕE�('�=|�{Pv�b��UǗ�HT�Yq'���܆2�e2���1� /"QA��S& � � The similar reaction of 3a or 4 led to 2α-amino-5α-cholestan-3-one (11a), that may be trapped as N-formyl derivative. Tax calculation will be finalised during checkout. Lyle, R. E., & Lamittina, J. L. (1974). Merck Index (pp. [2][3] volume 66, pages772–778(2012)Cite this article. The apparatus for the reduction was the same as described by Levene and Allen for the reduction of esters. DOI: 10.1021/jo00182a023. 0000001397 00000 n Depending on the nature of the additive and the temperature, chemoselective reduction of a nitro group in the presence of a ketone or an alkyne was possible. https://doi.org/10.2478/s11696-012-0195-6, DOI: https://doi.org/10.2478/s11696-012-0195-6, Over 10 million scientific documents at your fingertips, Not logged in Thermodynamic properties of substances The solubility of the substances Periodic table of elements. Synthesis of the male ant pheromone (E)-2,4-dimethyl-2-hexenoic acid was performed using this simple methodology. Ultrasonically activated reduction of substituted nitrobenzenes to corresponding N-arylhydroxylamines. Journal of the Chemical Society, 1945, 646–657. Learn more. Journal für Praktische Chemie, 342, 348–354. Tsukinoki, T., & Tsuzuki, H. (2001). Unlimited viewing of the article/chapter PDF and any associated supplements and figures. Zinc react with acetic acid to produce zinc acetate and hydrogen. (1959). Physical Data: see entries for 0000000644 00000 n DOI: 10.1002/(SICI)1521-3897(200004)342:4<348::AID-PRAC348>3.0.CO;2-6. A detailed mechanism illustrating the reduction of a nitro to an amine using zinc (Zn). trailer << /Size 41 /Info 24 0 R /Encrypt 29 0 R /Root 28 0 R /Prev 33593 /ID[<8adc52e84612fc5071a77be460cf2e8d><622a2a8ab052150353885e0e7d8d6ee7>] >> startxref 0 %%EOF 28 0 obj << /Type /Catalog /Pages 26 0 R /Metadata 25 0 R /PageLabels 23 0 R >> endobj 29 0 obj << /Filter /Standard /R 2 /O ( U�V�.�`�����Dz�-���#_m�_�}�g) /U (�!p�,��]za낭��2] Rl��=���) /P -4 /V 1 /Length 40 >> endobj 39 0 obj << /S 64 /L 104 /Filter /FlateDecode /Length 40 0 R >> stream 1. Working off-campus? For example, one could use: Hydrodenitration (replacement of a nitro group with hydrogen) is difficult to achieve but can be effected by catalytic hydrogenation over platinum on silica gel at high temperatures. 9536). Use the link below to share a full-text version of this article with your friends and colleagues. Form Supplied in: although zinc is available in a variety of forms, the overwhelming majority of zinc–acetic acid reductions use zinc powder. O’Neil, M. J. This is a preview of subscription content, log in to check access. Journal of Organic Chemistry, 24, 1214–1219. DOI:10.1139/v05-071. Kumar, P.S., Lokanatha Rai, K.M. Pap. This procedure is also a new method for the activation of zinc for electron transfer reduction of aromatic nitro compounds. Tetrahedron Letters, 25, 3415–3418. Acetic Acid. 6398). The reaction can also be carried out with zinc dust and ammonium chloride[citation needed]: Nitro compounds are typically reduced to oximes using metal salts, such as stannous chloride[26] or chromium(II) chloride. A mild, environmentally friendly method for reduction of aromatic nitro group to amine is reported, using zinc powder in aqueous solutions of chelating ethers. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, By continuing to browse this site, you agree to its use of cookies as described in our, This is an outdated version. Whitehouse Station, NY, USA: Merck Research Laboratories. Synthesis of (3-aminophenyl) acetylene via hydrogenation of (3-nitrophenyl)acetylene over cobalt polysulfide and ruthenium sulfide catalysts. DOI: 10.1021/cr010338r. Ho, T. L., & Wang, C. M. (1974). 2020-11-15. Working off-campus? Chemical Reviews, 85, 129–170. O’Neil, M. J. DOI: 10.1021/jo01335a011. DOI: 10.1021/cr60281a003. InChI = 1S/C2H4O2/c1‐2(3)4/h1H3,(H,3,4) Chemical Reviews, 62, 19–40. Zinc-catalyzed ammonium-formate reductions: Reduction of nitro compounds. Nitro groups in thiophene ring systems have been transformed directly to Harlow, UK: Longman. If you have previously obtained access with your personal account, please log in. (2006c). Hazlet, S. E., & Dornfeld, C. A. Zinc-promoted reduction of 2-(bromomethyl)alkenoates derived from Baylis–Hillman adducts gave (E)-2-methylacrylates in good yield and high stereoselectivity. 1589-1596, Reduction of 2-Nitro-5α-cholestan-3-one, Its Enol Tautomer and 2-Nitro-5α-cholest-2-en-3-amine Derivatives. p���&�N endstream endobj 40 0 obj 89 endobj 30 0 obj << /Type /Page /Parent 26 0 R /Resources 31 0 R /Contents 36 0 R /MediaBox [ 0 0 595 842 ] /CropBox [ 0 0 595 842 ] /Rotate 0 >> endobj 31 0 obj << /ProcSet [ /PDF /Text ] /Font << /F1 33 0 R /F2 32 0 R /F3 34 0 R >> /ExtGState << /GS1 37 0 R >> /ColorSpace << /Cs6 35 0 R >> >> endobj 32 0 obj << /Type /Font /Subtype /Type1 /Encoding /WinAnsiEncoding /BaseFont /Times-Roman >> endobj 33 0 obj << /Type /Font /Subtype /Type1 /Encoding /WinAnsiEncoding /BaseFont /Times-Italic >> endobj 34 0 obj << /Type /Font /Subtype /Type1 /Encoding /WinAnsiEncoding /BaseFont /Times-Bold >> endobj 35 0 obj [ /ICCBased 38 0 R ] endobj 36 0 obj << /Length 2579 /Filter /FlateDecode >> stream

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