Sodium Iodide → 7-chloro-3-(3,5-dimethylphenyl)-4-[2-(1-methylpiperidin-2-yl)-ethoxy]-6-nitro-1H-quinolin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (100 mg) and sodium bicarbonate (54 mg) was suspended in 2 mL dry N,N-dimethylformamide and heated to 80° C. on an oil bath. After 30 minutes, sodium iodide (48 mg) was added followed by 2-(2-chloroethyl)-1-methylpiperidine hydrochloride (64 mg) and the mixture stirred at 80° C. for 7 hours. At this time the reaction was cooled to room temperature and quenched by the addition of 25 mL ice/water. The mixture was filtered and the residue washed (1×) with ice water then dried at 40° C. Purification of the crude product by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 95:5) gave the title compound (67 mg).

Provenance & Evidence