Toluene → HCID 23498077, compound

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of 0.3 g (1.01 mmol) of 6-methoxy-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carbonitrile in 5 mL of phosphorus oxychloride is heated at 105° C. for 45 minutes. After cooling, the mixture is concentrated to dryness in vacuo to give a brown solid. To this is added 5 mL toluene, and the solution is concentrated to dryness again. Dropwise, an ice-cooled saturated aqueous sodium carbonate solution is added to the residue. This mixture is extracted with 5×25 mL of a 95:5 mixture of methylene chloride/methanol. The organic layer is dried over magnesium sulfate. The magnesium sulfate is removed by filtration, and solvent is removed in vacuo to provide 0.255 g of 4-chloro-6-methoxy-7-(4-methylpiperazin-1-yl)-quinoline-3-carbonitrile as a yellow solid, mp 177-179° C.

Provenance & Evidence