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Natural Science Forum / Chemistry / Organic Synthesis / April 2005Selective Reduction of nitro group
Could anyone give a good suggestion about the selective reduction of nitro group. My compound also contains an aldehyde group. I tried Fe/AcOH, it doesn't work well. Thanks  SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA My be sodium sylphide - polysylphide > Could anyone give a good suggestion about the selective reduction of > nitro group. My compound also contains an aldehyde group. I tried > Fe/AcOH, it doesn't work well. Thanks SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA > Could anyone give a good suggestion about the selective reduction of > nitro group. My compound also contains an aldehyde group. I tried > Fe/AcOH, it doesn't work well. Thanks hydrogenation conditions with Pd-C are best.. often no need for any pressure SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA john england wrote: > On 8 Sep 2004 14:13:40 -0400, xxy wrote: > > > Could anyone give a good suggestion about the selective reduction of > > nitro group. My compound also contains an aldehyde group. I tried > > Fe/AcOH, it doesn't work well. Thanks Try to use Zn/ammonium formate or Zn/ammonium chloride reducing system. try with Na in amonia.its safe for aldehyde group but if it does not work good enough then protect aldehyde group with ethyl glikol HOCH2-CH2OH . glikol protect C=O.then reduct your molecule.and atlast use some weak acid to deprotect carbonyl group. wish do best ;-) try with Na in amonia.its safe for aldehyde group but if it does not work good enough then protect aldehyde group with ethyl glikol HOCH2-CH2OH . glikol protect C=O.then reduct your molecule.and atlast use some weak acid to deprotect carbonyl group. wish do best ;-) would it be a valid reduction of NO2 reacting with (Hg) Zn, HCl Clemminson Reduction, like in a benzene substitution reaction: HNO3, H2SO4 for nitration of the benzene; Clemminson Redux. selectively reduce the Nitro group to an amine. john england wrote: > On 8 Sep 2004 14:13:40 -0400, xxy wrote: > > > Could anyone give a good suggestion about the selective reduction of > > nitro group. My compound also contains an aldehyde group. I tried > > Fe/AcOH, it doesn't work well. Thanks [quoted text clipped - 6 lines] > Georgia State University <chepjf@panther.gsu.edu> > Atlanta, GA Yes, it would. This process would also reduce any other easily reducible groups as well (like ketones). Not to say that H2/Pt wouldn't do the same. |
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