Hello,

what do you want to reduce it to? If you're looking to reduce it to an amino group, hydrogenation over Pd/C, PtO2 or Raney-Nickel should work fine. However, it depends on which other functional groups you have in your molecule. The Bechamp reduction (Iron and HCl) might be a better alternative.

Regards, 

JR

Could you write me please prosedure?

İron and HCl I tried but not achived

Hi,

Here's a general procedure:

Add EtOH, nitro compound (1 eq) and Fe powder (4 eq) in a two-necked round bottom flask equipped with a condenser and dropping funnel. Stir the mixture, heat to 60 degrees in an oil bath, and add concentrated HCl via the dropping funnel during approx. 30 minutes. Reflux the mixture for 1 hour to form the Ar-NH3+ ion.

Allow the reaction mixture to cool down and pour it into a flask containing distilled water, and then neutralize with a dilute NaOH solution to form Ar-NH2. Extract 3 times gently (!) with EtOAc to avoid trouble with iron hydroxides which easily cause emulsions...which can make phase separation take looong. Combine the EtOAc layers and dry over anhydrous Na2SO4, filter off the drying agent and evaporate under reduced pressure. Check the purity,purify if needed and analyze the final product by NMR.

You could also use Sn instead of Fe, but the extraction might be more complicated.

If you have other functional groups in your molecule, a reduction procedure using Fe/CaCl2 (reference below) could be of interest. This system seems to tolerate  halides and different carbonyls well.

Chandrappa, S.; Vinaya, T.; Ramakrishnappa, T.; Rangappa, K. S. Synlett, 2010, 3019-3022

For the catalytic hydrogenation in a reactor/autoclave, MeOH (or EtOH), 50 degrees, 10% Pd/C (premoistened with the chosen alcohol) and 2-6 bar H2 could be suitable. After the reaction, Pd/C is removed by filtration with gentle suction through a thin layer of celite, but make sure Pd/C doesn't get dry as it's pyrophoric...! Keep rinsing with MeOH/EtOH to wash the catalyst and celite. Evaporate the filtrate under reduced pressure and analyze the residue. Purify if needed and analyze by NMR.

Regards,

JR