Pyridine → 4-Iodo-N-methoxy-N-methyl-benzamide

Participants

Reaction Steps

A solution of pyridine (104 g, 1.32 mol) in dichloromethane (150 ml) was added dropwise to a suspension of 4-iodobenzoyl chloride (251 g, 0.94 mol) and N,O-dimethylhydroxylamine hydrochloride (97 g, 0.94 mol) in dichloromethane (850 ml) at 0° C. The mixture was allowed to warm to room temperature and was stirred for 18 hours. The solution was evaporated under reduced pressure, the residue was dissolved in ethyl acetate (1 l), and was then washed with dilute hydrochloric acid (2N, 3×400 ml) and saturated sodium bicarbonate solution (300 ml) and dried (Na2SO4). The organic extract was evaporated under reduced pressure. The residue was purified by distillation to yield the subtitle compound (241 g, 93%) as a yellow oil, b.p. 130° C. (0.1 mm Hg), which was characterized by 1H NMR.

Provenance & Evidence