Phosphorus oxychloride → 2-Chloro-3-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

3-Nitroquinolin-2(1H)-one (1.40 g, 7.36 mmol) obtained in Step 1 was dissolved in phosphorus oxychloride (3.50 mL, 36.8 mmol) and the mixture was stirred with heat at 110° C. for 4 hours. The reaction mixture was poured into an ice bath and thereby the reaction was stopped. Then, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 50/1) to give 2-chloro-3-nitroquinoline (1.46 g, yield: 95%).

Provenance & Evidence