Sodium dithionite is specific for nitro regardless of the ketone or other functions

SnCl2.2H2O (5 eq.) in EtOAc is what I always use.

At 50•C

You may protect the keto group by acetal formation with glycol in presence of traces of PTSA as catalyst in refluxing benzene and then reduce the nitro group by any usual reducing agent.

Stannous chloride is the reagent of choice in this case as it's very selective to the aromatic nitro group

KOH and Hydrazine hydrate this will reduce only nitro compound in presence of other reducible groups.

Thanks for your suggestion

hope i'll get desired product.

dear Mr. Singara

can you share a detail procedure i.e literature for refrence.

thanks in advance.

Sodium dithionite is specific for nitro regardless of the ketone or other functions

These are reference for the reduction of Nitro in presence of ketones....

http://www.sid.ir/en/VEWSSID/J_pdf/84320115806.pdf

http://pubs.acs.org/doi/pdf/10.1021/jo00124a043

This is also another reference for reduction but its based on solid support like Pegylated silica http://www.sid.ir/en/VEWSSID/J_pdf/84320115806.pdf

These are reference for the reduction of Nitro in presence of ketones by sodium dthionates....

http://www.organic-chemistry.org/chemicals/reductions/sodiumhydrosulfite-sodiumdithionite.shtm

In the presence of other reducible groups like - CH =CH2 or - CHO etc. on the ring, the nitro group may be selectively reduced to amino group using alkaline FeSO4. ( 5. Selective Reduction of Nitro group see page number 17)

http://nsdl.niscair.res.in/bitstream/123456789/796/1/Revised+organic+compounds+containing+Nitrogen.pdf

SnCl2 as well as Fe/NH4Cl or FeSO4 produce so much waste despite gives good selectivity. Sodium ditionite is also highly selective but very rarely gives good yields. Often is slightly more then 50%.

Really good point to protect keto-group with glycol and use whatever you want. Protection goes smoothly and take not so much time.

H2 as reducing agent in this case also acceptable due to wasteless.

Hydrazine hydrate reacts very fast with ketones to form hydrazones. And with KOH gives reduced ketone to alkane (Wolff-Kishner reduction)

You can practically reduce your nitro-aromatic compound in aqueous solvent within 1h.

First, dissolve your nitro compound in MeCN/water mixture (3:1 v/v) and add Nickel acetate (hydrated or not) to the nitro solution...chilled to 0 deg C. Wait 10-15 min while string of course. Add 3 equiv. of NaBH4 portion wise (very slowly). After the addition, allow the reaction flask to sit at rt for 30-45 min...your reaction is completed with more than 90% yield. All other functional group are safe!

Good luck

Aluminum amalgam easily prepared from aluminum foil and mercuric chloride aqueous solution may will worth a try with TLC control

Surprised the Fe/NH4Cl reduces your product elsewhere as it's usually quite selective. Not surprised for the hydrogenation though as alkenes and alkynes reacts quite quickly too.

I think as Pavlo Nikolaienko that you'll do a Wolff-Kishner reduction of your ketone with Hydrazine/KOH (and you just can't reoxidise that easily...).

If it's ketone reduction you observe with your iron reduction, I'd just reoxidize the sec-OH afterwards. Protection/deprotection is 2 steps - reoxidation is one...IBX/DMSO 2M. Add same amount of water and filter IBX. Extract with water/Et2O to remove DMSO. Product is usually super clean and yield is >95% (done that about 20 times in the past 2 years, benzaldehydes and dialkylketones worked just great...).

If it's alkene reduction (if you have an en-one, so conjugated double bond), now I'd go with ketone protection to deactivate that double bond and I'd try the iron or SnCl2 reduction again.

Sncl2/EtOH /HCl reflux

Did you try NH2-NH2? Check some literature. It worked for me for the reduction of aromatic nitro to amine. I am not sure about the reactivity of this (hydrazine) with ketones.

Reduction of nitro to amines with sodium hydrosulfite

The nitro compound was dissolved in acetone (3 mL/mmol) and aqueous NaOH (0.5 N, 5 eq). Excess sodium hydrosulfite was added and the reaction was refluxed for 1 h. If reaction is incomplete add more Na2S2O4 and aqueous NaOH. When all of the nitro starting material is consumed, the acetone is evaporated. The residue is taken up in ethyl acetate and washed with water, brine, and dried over MgSO4, filtered, and concentrated to give the crude amine.

Thank you all for your valuable suggestions.

Use NH2NH2/FeCl3 and Methanol:water (2:2) feflux it and then added ur compound

you can use NaSH or sodium polysulfhide, with this reagent you can obtain selectivity even of a nitro group in the presence of another. Check this link:

http://www.scribd.com/doc/102683462/Preparation-of-M-nitroaniline-From-Sodium-Polysulfide#scribd

Or this article by selective hidrogenation:

http://www.mdpi.com/2073-4344/4/3/276/

I also attached a publication that you can check for selected ammonolysis of nitro compounds

Article ChemInform Abstract: Preparation of Nitroanilines by Ammonol...