Methyl iodide → HCID 67106353, compound

Participants

Reaction Steps

From 4-nitrophenol by etherification with bromoacetic acid in the presence of sodium hydride in THF, acid chloride formation with thionyl chloride and catalytic DMF and amide formation with 2-amino-4,6-dimethylpyridine in triethylamine and chloroform to give N-(4,6-dimethyl-pyridin-2-yl)-2-(4-nitro-phenoxy)-acetamide. The amide is the reduced with borane-dimethylsulfide in THF at reflux, the resulting amine methylated with methyl iodide in the presence of sodium hydride in THF, and finally catalytic hydrogenation over Raney nickel in methanol gives the required aniline.

Provenance & Evidence