Chlorosulfonic acid → HCID 90419143, compound

HRID 2202356Notes

Reaction equation

HRID 2202356 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([S:13]([Cl:12])(=[O:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1605322-Fluoroquinoline

Product 1

HCID 90419143HCID 90419143, compound

Procedure

A solution of 2-fluoroquinoline (1.3 g, 8.9 mmol) in chlorosulfonic acid (15 mL) was stirred at −5-0° C. for 15 minutes and at 130° C. overnight. The resulting reaction mixture was poured into an ice-water mixture (300 mL), stirred at room temperature for 20 min, and extracted with EtOAc. The organic layer was then washed with brine, dried over Na2SO4 and solvent was removed. The residue was purified by column chromatography using a gradient elution from 100% PE to PE/EtOAc (100:6) to afford 1.1 g of title compound. 1H NMR (CHLOROFORM-d) δ: 8.56 (d, J=7.5 Hz, 1H), 8.43 (t, J=8.3 Hz, 1H), 8.25 (d, J=8.3 Hz, 1H), 7.72 (t, J=7.8 Hz, 1H), 7.32 (dd, J=8.9, 3.0 Hz, 1H). LC-MS: m/z 246.3 (M+H)+

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe organic layer was then washed with brine
  4. dry with materialdried over Na2SO4 and solvent
  5. customwas removed
  6. customThe residue was purified by column chromatography
  7. washa gradient elution from 100% PE to PE/EtOAc (100:6)

Sources & evidence

ORD record
ord-cbf72242d1494059a23f022c797d7b32
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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