Chlorosulfonic acid → HCID 90419143, compound

HRID 514820Notes

Reaction equation

HRID 514820 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-dc1d71507b404ae3b3dc77da749251a5
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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