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+ Pharma
+ Heterocyclic compounds
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Posted by
Al Grayson

Which reagent can reduce a nitro group to a primary amine but not...

Chamari B.S. Rajapaksha  Follow

Sorry hydrogen it should be


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Anunley117  Follow
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David A Miller  Follow

Hydrogenation all the way…. :) Use a balloon of hydrogen with your compound in ethyl acetate and Lindlar's catalyst. Leaves ketones and even most double bonds intact….
Also, SnCl2 would be a classic that is cheap, easy and rarely fails to perform.


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Charles Barfield  Follow

Typical reducing agents include, Fe / H+, Sn / H+ or catalytic hydrogenation (e.g. H2 / Pd)


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Albert Donnay  Follow

 To reduce a nitro group to a primary amine but not reduce ketones, you can use Fe in HCl or H2/PtO2 catalyst.

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Costa Conn  Follow

Which condition  help to reduce the cost, waste, environmentally friendly.
Your suggestions welcome. 

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Barry F  Follow

Dear Maiada,
the simplest way might be to protect keto carbonyl via oxime, hydrazone or aminoguanidine derivative formation /you may use NH2OH.HCl, H2N-NH2 or H2N-NH-/C=NH/- NH2.H2SO4. If your compound is not solubile in water, use less polar solvent, e.g. ethanol or methanol prior to reaction with the above mentioned reagents
Then you may reduce C-NO2 of the derivative using Fe powder/water solution of H2SO4. You might also use Zn/solution of H2SO4 reducing agent. Reduction should not be performed at elevated temperature, not to cause hydolysis of the prepared amino-derivative. I wonder wether Schulz-Tieman reduction /FeCl2 - HCl/ would not do for reduction of the nitro group.
When reduction is over you shall have to separate your product and submitt it to acid hydrolysis at increased temperature to obtain your expected keto-amine moiety.
Good luck,
R.S.


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Cathy Cintolo  Follow

 To reduce a nitro group to a primary amine but not reduce ketones, you can use Fe in HCl or H2/PtO2 catalyst.

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Bob Spillman  Follow

The reagent can reduce a nitro group to a primary amine but not reduce ketones, you can use sodium sulphide.

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Christopher Burgess  Follow

One can use Fe in HCl to reduce Nitro group in presence of ketone oR H2/Pt


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