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

hydroxylamine Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula . The compound exists as hygroscopic colorless crystals.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Prof ...

used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis. It is commercially available as its hydrochloride salt.

Synthesis

It may be prepared by reacting

ethyl chloroformate Ethyl chloroformate is an organic compound with the chemical formula . It is the ethyl ester of chloroformic acid. It is a colorless, corrosive and highly toxic liquid. It is a reagent used in organic synthesis for the introduction of the ethyl c ...

(or similar) with

followed by treatment with a

methylating agent Methylation, in the chemical sciences, is 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 term ...

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.

References

{{DEFAULTSORT:Dimethylhydroxylamine, N,O- Hydroxylamines Methyl compounds

Synthesis

See also

References