Dimethylamine → HCID 54565315, compound

Participants

Reaction Steps

A mixture of o-nitrophenol (1.0g, 7.19 mmoles), 37% aqueous formalin solution (0.81 ml, 10.78 mmoles) and 25% aqueous dimethylamine solution (1.9 ml, 10.78 mmoles) in 25 ml absolute ethanol was refluxed overnight and the volatile components then removed on a rotary evaporator. The resulting residue was chromatographed on silica gel (silica Woelm® 32-63 μ from Universal Scientific Inc.) using 5% methanol in methylene chloride as the eluent. The first major yellow band to elute contained 0.3g (23% yield) of 4-dimethylaminomethyl-2-nitrophenol. The next yellow band to elute contained 0.3g (23% yield) of the isomeric product, 2-dimethylaminomethyl-5-nitrophenol. The bismannich product remained on the column. The same results were obtained by using N,N,N',N'-tetramethyldiaminomethane instead of the dimethylamine and formalin.

Provenance & Evidence