N-Iodosuccinimide → HCID 68285982, compound
Reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7]([I:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
In a 3 L eggplant-shaped flask containing a stir bar, 7,8-difluoroquinoline (185.5 g, 1.12 mol), N-iodosuccinimide (505.4 g, 2.25 mol), and acetic acid (927 mL) were introduced and the mixture was stirred for 30 hours at 90° C. After cooling, the precipitated crystals was filtered and dried. On the other hand, the filtrate was concentrated under reduced pressure, the residual acetic acid was neutralized with sodium hydrogen carbonate, and the resultant was subjected to extraction with ethyl acetate. In addition, after the filtrate was dried with magnesium sulfate, filtered and concentrated, the thus obtained crude product was purified by silica gel column chromatography (normal hexane:ethyl acetate) to obtain 227.2 g (70%) of 7,8-difluoro-3-iodoquinoline was obtained as a hazel solid combined with the previously obtained crystals.
Workup
- additionIn a 3 L eggplant-shaped flask containing a stir bar
- temperatureAfter cooling
- filtrationthe precipitated crystals was filtered
- customdried
- concentrationOn the other hand, the filtrate was concentrated under reduced pressure
- extractionthe resultant was subjected to extraction with ethyl acetate
- dry with materialIn addition, after the filtrate was dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe thus obtained crude product
- customwas purified by silica gel column chromatography (normal hexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-bcad5431f40e4f55b2f07caf664d8a37
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772200B2
Reaction notes
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