Sodium Bisulfite → 7-Fluoro-2,3-dihydro-1h-indol-2-one

HRID 1045039

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH:7]2SC.S(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2

Participants

Conditions

Temperature: 25 °C

Procedure

7-Fluoro-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one (270.5 g) was dissolved in water (2000 g) and admixed with sodium bisulfite (300 g). The mixture was heated to reflux, in the course of which it was vigorously stirred. After 2.25 h, the mixture was cooled to 25° C. and isolated by filtration on a suction filter. It was washed twice with water (500 g each time) and then dried under reduced pressure (<50 mbar, 50° C.). This gave 7-fluoro-1,3-dihydro-2H-indol-2-one as a white solid (206.3 g, 95.1% by weight, 95% yield).

Workup

temperatureThe mixture was heated
temperatureto reflux, in the course of which it
customisolated by filtration on a suction
filtrationfilter
washIt was washed twice with water (500 g each time)
customdried under reduced pressure (<50 mbar, 50° C.)

Sources & evidence

ORD record: ord-55c6420b1cdb4957ae254223264664a4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563749B2

Linked notes

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