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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: wisconsinium on September 18, 2012, 11:54:16 AM

Title: nitro reduction
Post by: wisconsinium on September 18, 2012, 11:54:16 AM

Good morning,
I am brainstorming some reactions and am unsure about some functional group compatibilities. As shown in the scheme, I want to reduce a nitro group in the presence of an alpha-keto ester. How stable is the alpha-keto ester in general? Anything I need to look out for in this transformation? I am worried that it might destroy the alpha-keto ester or somehow cyclize the product. Thanks

Title: Re: nitro reduction
Post by: discodermolide on September 18, 2012, 12:04:41 PM

I think you should isolate the amine as a salt, i.e. do the reduction under acidic conditions, then you will avoid problems with the ketone and the ester.

Title: Re: nitro reduction
Post by: Schrödinger on September 18, 2012, 01:59:47 PM

We probably cant use Sn/HCl due to the presence of other active reducible groups. But when there are 2 nitro groups, we usually use NaSH. Is that applicable here? Can it selectively reduce the nitro group?

Title: Re: nitro reduction
Post by: OC pro on September 19, 2012, 10:10:51 AM

Like disco said Pd/C as catalyst in H2-atmosphere under acidic conditions. But cyclization can be very fast in this case.

Title: Re: nitro reduction
Post by: DrCMS on September 19, 2012, 10:50:03 AM

What about Bechamp reduction?

Title: Re: nitro reduction
Post by: OC pro on September 19, 2012, 01:28:45 PM

Should also work (Fe + HCl). Zn and Sn instead of Fe and HOAc instead of HCl will also be fine.