ORGLIST:Nitrogroup reduction

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From: Maringanti Krishna (maringanti9$##$
Date: Thu May 06 2004 - 08:49:53 EDT

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?

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