Your assumption about TMS coming off with SnCl2 is probably correct. Assuming that your substrate doesn't have an olefin or arylhalide, you can reduce the nitro group by hydrogenation with Pd, Pt, or RaNi catalysts. BH3 (DMS or Et2O complexes) should also work.

Reduction of NO2 with Sn/SnCl2 is normally carried out in acid conditions, in neutral conditions the reaction would be quite slow and, as David has indicated, your TMS group will suffer. If your NO2 is aryl rather than alkyl - you could try NaBH4 with Pd catalyst. If you look up the preparation and analysis of paracetamol on line - you will come accross a RSC educational publication which describes a procedure for the reduction of p-nitrophenol to p-aminophenol under quite mild conditions. Depending on what else is on your substrate, you may find this adaptable to your needs. If you need me to find and send you the link just ask.

Use TBDMS instead of TMS and probably it will wit6hstand your reaction conditions. Anyway, without seen themolecule it is difficult to make forecasts.

Kumar,

You may use N2H4 with Ni catalyst in ethanol, see

--- Prostakov, N. S. et al Khimiya Geterotsiklicheskikh Soedinenii, (11), 1528-31; 1985.

Or

use ammonium formate with Pd catalyst in methanol, see

---  Kimes, Alane S. et al  J. Med. Chem.  35(25), 4683-9; 1992.

Good luck

Dear Kumar,

is there any chance that you can have the protected amine beforehand which then would have to be unmasked under conditions suitable not to touch TMS?

Beside the latter is quite unstable and as suggested i would use TBDMS...