Iodine → HCID 67513815, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3′-amino-4′-ethyl-2-methylbiphenyl-4-carboxylate (1.1263 g, 4.18 mmol) and iodine (0.258 ml, 5.02 mmol) were mixed in chloroform (40 mL) and immersed in a preheated oil bath (90° C. when immersed). To this hot mixture was added n-amyl nitrite (0.668 ml, 5.02 mmol). The reaction mixture was heated in an 80° C. oil bath for 2 hours then allowed to cool to ambient temperature overnight. The crude was stirred with a Na2S2O3 solution. Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated. The resulting mixture was purified by flash chromatography (SiO2, Isolute Flash Si; 100 g). The column was eluted by an EtOAc/hexane mixture (0% to 30%). Related fractions were pooled and evaporated to afford a light yellow solid as the titled compound. LCMS calc.=380.03. found=381.09 (M+H)+.

Provenance & Evidence