Phosphorus oxychloride → 4-chloro-3-cyano-7-(3-morpholin-4-ylpropoxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinoline

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Reaction Steps

A mixture of 3-cyano-4-hydroxy-7-(3-morpholin-4-ylpropoxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinoline (500 mg) and phosphoryl chloride (2.5 ml) in acetonitrile (1.5 ml) was refluxed and stirred for 4 hours. After cooling, the solution was evaporated to dryness. The flask containing the residue was filled with ice chips and excess concentrated aqueous ammonia (25 ml) was added. This mixture was allowed to warm up while stirring overnight. The product was filtered off and air-dried. The title compound was obtained as a white solid (480 mg, 92%); Mass spectrum: M+H+ 432.

Provenance & Evidence