Re: ORGLIST:Nitrogroup reduction

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From: Fredrik Thorstensson (freto$##$ifm.liu.se)
Date: Fri May 07 2004 - 03:00:06 EDT


Hi

You could try SnCl2*H20 in DMF. J.comb.chem, 2001, 546-553.

/FT

Maringanti Krishna wrote:

> Hi All:
> I need to reduce an aromatic nitro group to -NH2. It is a large
> molecule and I have an Acetal and t-BOC protections elsewhere. I have
> tried the following methods.
> 1. Raney Nickel, Hydrogenation: Several spots on TLC (after complete
> disappearance of starting material, and after 48 hours)
> 2. Pd/C Hydrogenation...very low yield after 48 hours
> 3. Pd/C hydrazine hydrate. Reaction is OK but, the yield is verylow.
> Difficult to get pure product. Also, acetal deprotection
> 4. Electrolytic iron/ ammonium acetate and ammonium chloride. Acetal
> deprotection is occuring. At rt. reaction is extremely sluggish. At
> reflux, acetal deprotection is taking place.
>
> Can someone suggest an alternative method?
> Krishna
>
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