Potassium Iodide → 2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (21.5 g, 0.106 mol) in acetonitrile (638 mL) was added cesium carbonate (72.4 g, 0.222 mol), potassium iodide (1.76 g, 0.011 mol) and then 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (35.23 g, 0.111 mol), the white slurry was stirred at room temperature for four hours at room temperature. Water (700 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to yield to of 2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [40.0 g; 86% of theory; HPLC/MS: m/z=440 (M+H); log P(HCOOH)=3.04].

Provenance & Evidence