Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies
A novel chemical synthesis and purification scheme to produce ANOT (3-amino-5-nitro-o-toluamide) was developed to yield an analytical standard grade material for zoalene residue investigations. An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature refe...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 1998-09, Vol.46 (9), p.3623-3629 |
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| container_end_page | 3629 |
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| container_issue | 9 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 46 |
| creator | Webster, Gregory K Pastore, Richard J Hawkins, Kenneth A Hirsch, Arnold L |
| description | A novel chemical synthesis and purification scheme to produce ANOT (3-amino-5-nitro-o-toluamide) was developed to yield an analytical standard grade material for zoalene residue investigations. An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature references were available for the partial reduction of dinitro aryl compounds, but none detailed the conversion of zoalene to ANOT. A chemical synthesis was chosen over a biological synthesis due to the latter's complex reaction matrix, difficult recovery, and low batch yields. Using general partial reduction of dinitro aryl schemes, it was found that 10% palladium on carbon coupled to a cyclohexene reducing agent provided an optimum ANOT yield. Chromatographic techniques were utilized to isolate ANOT from the product mixture and to purify it to a standard grade material (>99% pure). The chemically synthesized ANOT product was characterized using colorimetric, TLC, FTIR, NMR, and LC/MS techniques. Keywords: ANOT; zoalene; zoaline residue; chemical reduction |
| doi_str_mv | 10.1021/jf9802068 |
| format | Article |
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An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature references were available for the partial reduction of dinitro aryl compounds, but none detailed the conversion of zoalene to ANOT. A chemical synthesis was chosen over a biological synthesis due to the latter's complex reaction matrix, difficult recovery, and low batch yields. Using general partial reduction of dinitro aryl schemes, it was found that 10% palladium on carbon coupled to a cyclohexene reducing agent provided an optimum ANOT yield. Chromatographic techniques were utilized to isolate ANOT from the product mixture and to purify it to a standard grade material (>99% pure). The chemically synthesized ANOT product was characterized using colorimetric, TLC, FTIR, NMR, and LC/MS techniques. 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Psychology ; MEDICAMENT ; MEDICAMENTOS ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; PURIFICACION ; PURIFICATION ; REDUCCION ; REDUCTION ; RESIDU ; RESIDUES ; RESIDUOS ; SYNTHESIS</subject><ispartof>Journal of agricultural and food chemistry, 1998-09, Vol.46 (9), p.3623-3629</ispartof><rights>Copyright © 1998 American Chemical Society</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a346t-adaec4968e3e20d5f72e3b606dcdc1765ecebe04d9a0e9750d3f52f5d588f8ab3</citedby><cites>FETCH-LOGICAL-a346t-adaec4968e3e20d5f72e3b606dcdc1765ecebe04d9a0e9750d3f52f5d588f8ab3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf9802068$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf9802068$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2433501$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Webster, Gregory K</creatorcontrib><creatorcontrib>Pastore, Richard J</creatorcontrib><creatorcontrib>Hawkins, Kenneth A</creatorcontrib><creatorcontrib>Hirsch, Arnold L</creatorcontrib><title>Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>A novel chemical synthesis and purification scheme to produce ANOT (3-amino-5-nitro-o-toluamide) was developed to yield an analytical standard grade material for zoalene residue investigations. An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature references were available for the partial reduction of dinitro aryl compounds, but none detailed the conversion of zoalene to ANOT. A chemical synthesis was chosen over a biological synthesis due to the latter's complex reaction matrix, difficult recovery, and low batch yields. Using general partial reduction of dinitro aryl schemes, it was found that 10% palladium on carbon coupled to a cyclohexene reducing agent provided an optimum ANOT yield. Chromatographic techniques were utilized to isolate ANOT from the product mixture and to purify it to a standard grade material (>99% pure). The chemically synthesized ANOT product was characterized using colorimetric, TLC, FTIR, NMR, and LC/MS techniques. Keywords: ANOT; zoalene; zoaline residue; chemical reduction</description><subject>3-AMINO-5-NITRO-O-TOLUAMIDE</subject><subject>ANTICOCCIDIALS</subject><subject>ANTICOCCIDIEN</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>COCCIDIOSTATICOS</subject><subject>DINITOLMIDE</subject><subject>DRUGS</subject><subject>Exact sciences and technology</subject><subject>Feed and pet food industries</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>MEDICAMENT</subject><subject>MEDICAMENTOS</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>PURIFICACION</subject><subject>PURIFICATION</subject><subject>REDUCCION</subject><subject>REDUCTION</subject><subject>RESIDU</subject><subject>RESIDUES</subject><subject>RESIDUOS</subject><subject>SYNTHESIS</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><recordid>eNptkLtOwzAUhi0EEuUy8ABIHmBgCBzHseOMVcVNohS1KUIslmsfQ0pJKjuV4O0JCurEdIbvO7efkBMGlwxSdrX0hYIUpNohAyZSSARjapcMoIOJEpLtk4MYlwCgRA4Dcjd6x8_KmhWdotvYtmpq2nj62pgV1kjbhg4fJyX1TaDziLSqt2iKsXIbpLN24yqMR2TPm1XE4796SOY31-XoLnmY3N6Phg-J4ZlsE-MM2qyQCjmm4ITPU-QLCdJZZ1kuBVpcIGSuMIBFLsBxL1IvnFDKK7Pgh-Sin2tDE2NAr9eh-jThWzPQvxHobQSde9a7axO7F30wta3itiHNOBfAOi3ptSq2-LXFJnxomfNc6PJppmX5PH7J5Ysed_5p73vTaPMWupHzGSuKoguZ579rz3tubNTLZhPqLpB_zvsBvQh-SA</recordid><startdate>19980901</startdate><enddate>19980901</enddate><creator>Webster, Gregory K</creator><creator>Pastore, Richard J</creator><creator>Hawkins, Kenneth A</creator><creator>Hirsch, Arnold L</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19980901</creationdate><title>Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies</title><author>Webster, Gregory K ; Pastore, Richard J ; Hawkins, Kenneth A ; Hirsch, Arnold L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a346t-adaec4968e3e20d5f72e3b606dcdc1765ecebe04d9a0e9750d3f52f5d588f8ab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>3-AMINO-5-NITRO-O-TOLUAMIDE</topic><topic>ANTICOCCIDIALS</topic><topic>ANTICOCCIDIEN</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>COCCIDIOSTATICOS</topic><topic>DINITOLMIDE</topic><topic>DRUGS</topic><topic>Exact sciences and technology</topic><topic>Feed and pet food industries</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>MEDICAMENT</topic><topic>MEDICAMENTOS</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>PURIFICACION</topic><topic>PURIFICATION</topic><topic>REDUCCION</topic><topic>REDUCTION</topic><topic>RESIDU</topic><topic>RESIDUES</topic><topic>RESIDUOS</topic><topic>SYNTHESIS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Webster, Gregory K</creatorcontrib><creatorcontrib>Pastore, Richard J</creatorcontrib><creatorcontrib>Hawkins, Kenneth A</creatorcontrib><creatorcontrib>Hirsch, Arnold L</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Webster, Gregory K</au><au>Pastore, Richard J</au><au>Hawkins, Kenneth A</au><au>Hirsch, Arnold L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1998-09-01</date><risdate>1998</risdate><volume>46</volume><issue>9</issue><spage>3623</spage><epage>3629</epage><pages>3623-3629</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>A novel chemical synthesis and purification scheme to produce ANOT (3-amino-5-nitro-o-toluamide) was developed to yield an analytical standard grade material for zoalene residue investigations. An original conversion of zoalene (3,5-dinitro-o-toluamide) to ANOT was developed. Several literature references were available for the partial reduction of dinitro aryl compounds, but none detailed the conversion of zoalene to ANOT. A chemical synthesis was chosen over a biological synthesis due to the latter's complex reaction matrix, difficult recovery, and low batch yields. Using general partial reduction of dinitro aryl schemes, it was found that 10% palladium on carbon coupled to a cyclohexene reducing agent provided an optimum ANOT yield. Chromatographic techniques were utilized to isolate ANOT from the product mixture and to purify it to a standard grade material (>99% pure). The chemically synthesized ANOT product was characterized using colorimetric, TLC, FTIR, NMR, and LC/MS techniques. Keywords: ANOT; zoalene; zoaline residue; chemical reduction</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jf9802068</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 1998-09, Vol.46 (9), p.3623-3629 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | American Chemical Society Journals |
| subjects | 3-AMINO-5-NITRO-O-TOLUAMIDE ANTICOCCIDIALS ANTICOCCIDIEN Biological and medical sciences Chemistry COCCIDIOSTATICOS DINITOLMIDE DRUGS Exact sciences and technology Feed and pet food industries Food industries Fundamental and applied biological sciences. Psychology MEDICAMENT MEDICAMENTOS Noncondensed benzenic compounds Organic chemistry Preparations and properties PURIFICACION PURIFICATION REDUCCION REDUCTION RESIDU RESIDUES RESIDUOS SYNTHESIS |
| title | Chemical Reduction of Zoalene to ANOT for Use in Zoalene Residue Studies |
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