Re: ORGLIST:Nitrogroup reduction

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From: samarium Steiner (neptunium$##$gmx.net)
Date: Fri May 07 2004 - 05:48:23 EDT


See M. Petrini et al., Synth commun 1987, 713-4. There's used the following
system (seems to be nice and very smoothly): NaBH4 and Pd-C 10% in absolute
THF. so the H-source is NaBH4.

greets samarium

>
>
> 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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