资源描述：
《INDIUMAMMONIUM CHLORIDE-MEDIATED SELECTIVE.pdf》由会员上传分享，免费在线阅读，更多相关内容在学术论文-天天文库。
1、OrganicSyntheses,Vol.81,p.188-194(2005);Coll.Vol.11,p.57-61(2009).INDIUM/AMMONIUMCHLORIDE-MEDIATEDSELECTIVEREDUCTIONOFAROMATICNITROCOMPOUNDS:ETHYL4-AMINOBENZOATE(Benzoicacid,4-amino-,ethylester)In,NH4ClO2NCO2C2H5H2NCO2C2H5EtOH1SubmittedbyBimalK.Banik,IndraniBanik,andFrederickF.Becker.CheckedbyWeiq
2、iangHuangandMarvinJ.Miller.1.ProcedureEthyl4-aminobenzoate.A1000-mL,round-bottomedflaskequippedwithamagneticstirbarischargedwithasuspensionof10g(51mmol)ofethyl4-nitrobenzoatein250mLofethanol,andasolutionof27.4g(510mmol)ofammoniumchloridein125mLofwateristhenadded(Note1).Indiumpowder(23.5g,205mmol)(
3、Note2)isadded,andtheresultingmixtureisheatedatrefluxfor2.5hr.Thereactionmixtureisallowedtocooltoroomtemperature,dilutedwith350-400mLofwater,andfilteredundervacuum.Thefiltrateisextractedwith6-8portionsof50-60mLofdichloromethane,andthecombinedorganicphasesarewashedwith100mLofbrineanddriedoveranhydro
4、ussodiumsulfate.Theresultingsolutionisconcentratedunderreducedpressureandthecrudeproductisdissolvedin100mLofdichloromethane.Thesolutionisconcentratedbywarming,and50mLofhexaneisthenadded.Theresultingsolutionisallowedtostandinarefrigeratorovernightandthenfilteredundervacuumtogive7.63g(90%)ofethyl4-a
5、minobenzoate(Note3).2.Notes1.Ethyl4-nitrobenzoate,ammoniumchloride,ethanolwerepurchasedfromAldrichChemicalCompanyandusedasreceived.2.Indiumpowder(99.99%)wasobtainedfromAldrichChemicalCompany.1883.Thespectralpropertiesofethyl4-aminobenzoateareasfollows:IR-1(film)cm:3424,3345,3224,1685,1636,1598,151
6、5,1367,1312,1281,11173,773;HNMR(300MHz,CDCl3):1.36(3H,t,J=6),4.04(2H,13brs),4.31(2H,q,J=7),6.63(2H,d,J=9),7.85(2H,d,J=9);CNMR(75MHz,CDCl3):14.6(CH3),60.4(CH2),114.0(Ar-CH),120.5(Ar-q),131.7(Ar-CH),151.0(Ar-q),166.9(Ar-q=quaternarycarbonatom);m/e:+166(M+H);exactmass:m/e(M):165.0764(measured),165.
7、0790(theoretical).WasteDisposalInformationAlltoxicmaterialsweredisposedofinaccordancewiththepolicyofUTMDACCtohandleanddisposeofhazardouswaste,whichisinaccordancewiththeregulationsoftheEnvironmentalProtectionAgenc
