Nitrobenzene → 6-Iodoquinolin-3-ol

Participants

Reaction Conditions

Reaction Steps

3-hydroxy-6-iodoquinoline-4-carboxylic acid (22 g, 70 mmol) was suspended in 1-nitrobenzene (143 ml, 1397 mmol) followed by adding Hunig's base (25 mL)-the suspension was completely dissolved. The resulting mixture was heated to reflux (210° C.) under N2. After 3 h, LC/MS showed no sign of starting material mass. The reaction mixture was cooled to rt; solvent was removed as much as possible in vacuo. The crude product was redissolved in DCM/MeOH and the solid was collected by filtration. The solid was rinsed with hexane and either and dried as brownish solid. The filtrate was removed excess solvent and purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-058, 330 g SiO2, solvent system: hexanes:acetone=80%:20%, Flow=100 mL/min) to afford the desired product as brown solid. MS m/z: 272.3 (M+H). Calc'd. for C9H6INO−271.05.

Provenance & Evidence