N,O-Dimethylhydroxylamine

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N,O-Dimethylhydroxylamine[1]
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N,O-Dimethylhydroxylamine is a methylated hydroxylamine used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis.[2] It is commercially available as its hydrochloride salt.[1]

Synthesis

It may be prepared by reacting ethyl chloroformate (or similar) with hydroxylamine followed by treatment with a methylating agent such as dimethyl sulfate. The N,O-dimethylhydroxylamine is then liberated by acid hydrolysis followed by neutralization.[2]

File:N,O-Dimethylhydroxylamine synthesis01.svg

See also

References

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  1. a b N,O-Dimethylhydroxylamine hydrochloride at Sigma-Aldrich
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