ORGLIST: Reduction of N-nitroso-2-oxazolidinone

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From: antonio regla (areglac$##$
Date: Wed Jul 11 2001 - 13:13:50 EDT

Dear List members:

I would like to reduce N-nitroso-2-oxazolidinone with sodium dithionite to the N-amino-2-oxazolidinone, however the reaction conditions used for this type of reduction for n-nitrosoamines, aqueous NaOH/ethanol do not work for the N-nitroso-2-oxazolidinone. I am aware that sodium dithionite cannot be used in acid solutions, only in basic solution. I suspect that my compound is decomposing before any reduction takes place. Does anyone know of a reference or a procedure useful for reduction of n-nitrosocarbamates to n-aminocarbamates with sodium dithionite, also called sodium hydrosulfite? I know that zinc may effect this reduction, however, I would prefer to use the cheaper reagent. I would appreciate any help you may provide.


Antonio Regla

Universidad Autonoma de Morelos

Cuernavaca, Mexico

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