m-Chloroperbenzoic acid → 8-Chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine 3-oxide

Temperature

0 °C

To the stirred solution of 8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (1.0 g, 4.09 mmol), prepared as described in Example 2, Part C, in DCM (20 mL) cooled to 0° C. was added m-CPBA (1.763 g, 10.22 mmol). The reaction mixture was then warmed to ambient temperature and stirred for 4 h. Reaction mixture was then diluted with dichloromethane (100 mL) and washed with saturated sodium bicarbonate solution (200 mL), brine solution (50 mL). The organics were then dried over sodium sulphate, filtered and concentrate to afford 8-chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine 3-oxide (1.0 g, 3.84 mmol, 94% crude yield) as a yellow solid. The material was carried on without further purification. LC/MS (ESI) m/e 261.0, [(M+H)+, calcd for C13H10ClN2O2, 261.0]; LC/MS retention time (method C): tR=1.65 min.

1. temperatureThe reaction mixture was then warmed to ambient temperature
2. customReaction mixture
3. washwashed with saturated sodium bicarbonate solution (200 mL), brine solution (50 mL)
4. dry with materialThe organics were then dried over sodium sulphate
5. filtrationfiltered
6. concentrationconcentrate

ORD record

ord-6f9972397b674727bb576bc81ca08c47

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2