''N'',''O''-Dimethylhydroxylamine is a methylated

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

used to form so called 'Weinreb amides' for use in the

Weinreb ketone synthesis The Weinreb–Nahm ketone synthesis is a chemical reaction used in organic chemistry to make carbon–carbon bonds. It was discovered in 1981 by Steven M. Weinreb and Steven Nahm as a method to synthesize ketones. The original reaction involved ...

. It is commercially available as its

hydrochloride salt In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternative na ...

Synthesis

It may be prepared by reacting

ethyl chloroformate Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Preparation Ethyl chlorofo ...

(or similar) with

followed by treatment with a

methylating agent In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These te ...

such as

dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agen ...

. The N,O-dimethylhydroxylamine is then liberated by acid hydrolysis followed by neutralization. N,O-Dimethylhydroxylamine synthesis01

References

{{DEFAULTSORT:Dimethylhydroxylamine, N,O- Hydroxylamines

Synthesis

See also

References