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1,4-Dihydro-8-methoxy-4-oxo-3-quinolinecarbonitrile (3.8 g, 19 mmol) was used as a raw material, which was mixed with 40 mL of phosphoryl chloride and 5 drops of DMF and reacted at reflux for 0.5 hours. After completion of the reaction, the mixture was evaporated to dryness and the residue was diluted with hexane. Subsequently, the solid product was collected, mixed with cold dilute sodium carbonate solution and extracted several times with ethyl acetate. The organic layers were combined, dried with anhydrous sodium sulfate and filtered through a pad of silica gel. Finally, the solvent was removed under reduced pressure to afford 4-chloro-8-methoxy-3-quinolinecarbonitrile 3.8 g as an off-white solid in 91% yield. The product was analyzed by mass spectrometry (electrospray) and showed m/e: [M+H]+ 219.1.

[1] Patent: EP973746, 2003, B1. Location in patent: Page/Page column 85
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 24, p. 2825 - 2828
[3] Patent: EP1117659, 2003, B1. Location in patent: Page 66