m-Chloroperbenzoic acid → 6-Bromoisoquinolin-1(2H)-one

A solution of Intermediate 94 (1.04 g) in methylene chloride (3 ml) was added with a solution of 3-chloroperbenzoic acid (2.16 g) in methylene chloride (3 ml), and stirred for 20 hours. The reaction mixture was added with methylene chloride (200 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. A solution of the residue in acetic anhydride (10 ml) was refluxed by heating for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was added with 2.5 N aqueous sodium hydroxide (20 ml), and stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature, and neutralized with 5 N aqueous hydrochloric acid under ice cooling to obtain the precipitated title compound (Intermediate 95, 623 mg).

1. washwashed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
2. customThe organic layer was dried
3. customthe solvent was evaporated under reduced pressure
4. temperatureA solution of the residue in acetic anhydride (10 ml) was refluxed
5. temperatureby heating for 5 hours
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. additionthe residue was added with 2.5 N aqueous sodium hydroxide (20 ml)
8. stirringstirred at 100° C. for 1 hour
9. customto obtain the
10. customprecipitated title compound (Intermediate 95, 623 mg)

ORD record

ord-6a30c24e68ca4170913df323445122b8

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470807B2