Lithium hydroxide, monohydrate → HCID 70984088, compound

Participants

Reaction Steps

To a suspension of (E)-methyl 6-(2-((8-tert-butylquinolin-2-yl)methylene)hydrazinyl)nicotinate (1.78 g, 4.91 mmol) in DCM (40 mL) was added iodobenzene diacetate (1.90 g, 5.89 mmol). The reaction mixture was stirred at ambient temperature for 4 hours. The solvent was removed, and the resulting residue was suspended in 1:1 hexane/ether (50 mL) and stirred at ambient temperature for 10 minutes. The solid that formed was collected by filtration. The solid was then suspended in 1:1 THF/H2O (50 mL) and LiOH—H2O (0.82 g, 19.6 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 hours. THF was removed under reduced pressure. The resulting aqueous solution was acidified with saturated potassium hydrogen sulfate to pH˜3-4. The solid that formed was collected by filtration, washed with water, 1:1 hexane/ether (50 mL) and dried to give 3-(8-tert-butylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (1.55 g, 91.1%) as solid.

Provenance & Evidence