Trifluoromethanesulfonic anhydride → Trifluoromethanesulfonic acid 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl ester

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (1.0 g in 50 mL dry methylene chloride) was added 0.455 ml diazabicycloundecene and the mixture cooled to -78° C. To this was added trifluoromethanesulfonic anhydride (0.51 mL) dropwise via syringe and the mixture stirred at low temperature. After 1 hour, the reaction was quenched by the addition of saturated ammonium chloride (35 mL) and extracted with ethyl acetate (3×75 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2) gave the title compound (629 mg).

1. customthe reaction was quenched by the addition of saturated ammonium chloride (35 mL)
2. extractionextracted with ethyl acetate (3×75 mL)
3. washThe organics were washed with water (50 mL) and brine (50 mL)
4. dry with materialthen dried over magnesium sulfate
5. customPurification of the
6. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2)

ORD record

ord-59911d1c1743434daa7684f1673764f6

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147088