N,O-Dimethylhydroxylamine Explained

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

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.

See also

Notes and References

  1. Weinreb. Steven M.. Folmer. James J.. Ward. Timothy R.. Georg. Gunda I.. N,O-Dimethylhydroxylamine . E-EROS Encyclopedia of Reagents for Organic Synthesis. 2006. 10.1002/047084289X.rd341.pub2. 0471936235 .