Pyridine → HCID 11345498, compound

Participants

Reaction Steps

The intermediate N-methoxy-N-methyl-p-biphenylcarboxamide was first formed. Pyridine (4 mL, 5 equivalents) and N,O-dimethylhydroxylamine hydrochloride (980 mg, 10 mmol) were added to a solution of p-biphenylcarbonyl chloride (2.16 g, 10 mmol) in dry dichloromethane (10 mL). The solution was stirred for 2 hours at room temperature and then diluted with ethyl acetate (20 mL), washed sequentially with 1N HCl (2×20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL). It was then dried over magnesium surfate and evaporated under reduced pressure to give N-methoxy-N-methyl-p-biphenylcarboxamide as a solid (1.78 g, 74%). The solid was recrystallized from ethyl acetate/hexane for analysis: mp 77°-78° C. The identity of the solid was confirmed as that of N-methoxy-N-methyl-p-biphenylcarboxamide by IR, proton NMR, 13C NMR and elemental analysis, with mass spectrometric determination of the molecular weight.

Provenance & Evidence