Chlorosulfonic acid → 5-Fluoroquinoline-8-sulfonyl chloride

HRID 514823Notes

Reaction equation

HRID 514823 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[F:1][C:2]1[CH:11]=[CH:10][C:9]([S:13]([Cl:12])(=[O:15])=[O:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1152435-Fluoroquinoline

Product 1

HCID 177508995-Fluoroquinoline-8-sulfonyl chloride

Conditions

Temperature
130 °C

Procedure

5-fluoroquinoline (800 mg, 5.4 mmol) was added slowly to 10 mL of chlorosulfonic acid at 0° C. When the addition was complete, the reaction mixture was heated at 130° C. overnight. The solution was allowed to cool and was slowly poured over ice. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried and evaporated to give the crude product, which was purified by column chromatography (5% EtOAc/PE) to afford 400 mg of title compound. 1H NMR (CHLOROFORM-d) δ: 7.40 (t, J=8.46 Hz, 1 H), 7.74 (dd, J=8.60, 4.30 Hz, 1 H), 8.55-8.64 (m, 2 H), 9.32 (dd, J=4.30, 1.88 Hz, 1 H). LC-MS: m/z 4 246 (M+H)+

Workup

  1. additionWhen the addition
  2. temperatureto cool
  3. additionwas slowly poured over ice
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. customThe combined organic extracts were dried
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by column chromatography (5% EtOAc/PE)

Sources & evidence

ORD record
ord-28df3fd24a774d8b8d151bf138b914d1
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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