Hi,

Try the following conditions like in this paper:http://www.orientjchem.org/dnload/DAVOOD-SETAMDIDEH-BEHROOZ-KHEZRI-and-MANOUCHEHR-MOLLAPOUR/OJCV027I03P991-996.pdf

or NaBH4/sulphur/THF (Lalancette reduction). The last method can be applied to aromatic nitro cmpds with Cl, Br, COOR, CN or -CH=CR2.

Lit.:

Synthesis 1972, 526

Can.J.Chem. 1970 (48), 735.

Many methods of aromatic nitro cmpds reduction you can find in

Comprehensive Organic Transformations, A Guide to Functional Group Preparations, Two Volume Set, 2nd Edition

Richard C. Larock

ISBN: 978-1-118-03758-4

Sincerely,

AD

aromatic nitro group can be easily reduced to aromatic amine using Sn/HCl

I think you should utilize the nonocatalysts such as palladium or platin and reduction agents like NaBH4 to facilitates your reaction

See Ram, S.; Ehrenkaufer, R.E. Synthesis 1988, 91–94. Reduction is done on room temperature using ammonium formate and 10% Pd/C.

If you really need to avoid any use of metal, another possibility is dithionate: Hodgson H.H., Ward E.R., J. Chern. Soc. 1947, 327. However, this involves some heating. Lalancette reduction is also done on reflux.

Basically you can;t avoid both heating and use of metal catalysts.

If there's a baker nearby try out baker's yeast (Lit.: Tetrahedron Lett. 1997, 38, 3043).

General Procedure for Nitro Reduction with Stannous Chloride (ultrasonication)

To a solution of 1 (0.148 g, 0.967 mmol) in ethanol (5 mL) was added SnCl2.2H2O (2.26 g, 10.0

mmol). The reaction mixture was exposed to ultrasonic irradiation for 2 h at 30 °C until the reaction

was complete as indicated by TLC analysis. The solvent was removed under reduced pressure and

the crude residue was partitioned between ethyl acetate and 2M KOH. The aqueous layer was

extracted with further portions of ethyl acetate (3 x 25 mL) and the combined organic extracts were

washed with brine (2 x 25 mL) and water (3 x 50 mL), dried (MgSO4) and concentrated under

reduced pressure. The crude residue was subjected to flash silica gel column chromatography (20%

ethyl acetate in hexanes) yielding 3-methoxyaniline 2 (76%)

Lit: http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1174&context=scipapers

All, thank you for the response. I am aware of some of the best techniques to achieve this conversion, please add if you have other suggestions.

So far I think Bernhard's suggestion is the most intriguing one. Thank you Bernhard, I will read this first (and probably have to hunt for a local bakery). :)

You're welcome!

If yeast does not work you can check out other bioenzymatic reductions which might be more suitable for your system.

Hello,

There is a system descirbed involving catalytic Pt/C (sorry, it's a metal, but it'a catalytic) and ammonium formiate (I think in anhydrous ethanol but I am not sure, here is the original publication: D. Channe Gowda and B. Mahesh, Synthetic Commun., 2000, 30, 3639.

Good luck, Pierre

Hello,

What about just SnCl2:

http://www.sciencedirect.com/science/article/pii/S0040403901800411

Sincerely,

Kyle Grice

sodiumdithionite(Na2S2O3)5H2O,Methanol+water for nitro reduction

Usually phenyl nitro group can be easily reduced to aromatic amine using Sn/HCl only

Sodium dithionite is best for nitro reduction

You can use H2/Pt for reduction of NO2 group to amino group.