N,O-Dimethylhydroxylamine

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] 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]

Structural formula of N,O-dimethylhydroxylamine
Ball-and-stick model of the N,O-dimethylhydroxylamine molecule