Pyridine → Methyl [3-(3-bromopropoxy)anilino](oxo)acetate

Participants

Reaction Steps

A solution of 1.5 ml of oxalic acid monomethyl ester chloride in 10 ml of methylene chloride is added dropwise in the course of 10 minutes to a solution of 3.5 g of 3-(3-bromopropoxy)-aniline and 1.3 ml of pyridine in 40 ml of methylene chloride. After stirring for 2 hours at room temperature the mixture is poured onto water and extracted with methylene chloride. The combined extracts are concentrated by evaporation and the residue is chromatographed with methylene chloride/ethyl acetate (10:1) over silica gel. The eluate is concentrated by evaporation and the residue is crystallised from ether/hexane. N-[3-(3-bromopropoxy)-phenyl]-oxamic acid methyl ester having a melting point of 90°-91° is obtained.

Provenance & Evidence