Chlorosulfonic acid → 5-Fluoro-8-hydroxy-7-quinolinesulfonyl chloride

HRID 382891Notes

Reaction equation

HRID 382891 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[F:1][C:2]1[CH:11]=[C:10]([S:14]([Cl:13])(=[O:16])=[O:15])[C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 2179075-Fluoro-8-quinolinol

Product 1

HCID 183725065-Fluoro-8-hydroxy-7-quinolinesulfonyl chloride

Conditions

Temperature
0 °C

Procedure

A solution of 5-fluoro-8-hydroxyquinoline (0.50 g) in 4.0 mL of chlorosulfonic acid is stirred for 3 h at 90° C. and then 13 h at 105° C. The mixture is then cooled to 0° C. and poured onto 50 mL of finely divided −15° C. ice. The bright orange-red precipitate is collected by filtration, washed with four 10-mL portions of 0° C. distilled water and three 2 mL portions of diethyl ether, and dried in a stream of air to give 0.208 g of the title compound as a red-orange powder.

Workup

  1. custom13 h
  2. customat 105° C
  3. additionpoured onto 50 mL of finely divided −15° C. ice
  4. filtrationThe bright orange-red precipitate is collected by filtration
  5. washwashed with four 10-mL portions of 0° C.
  6. distillationdistilled water and three 2 mL portions of diethyl ether
  7. customdried in a stream of air

Sources & evidence

ORD record
ord-9224d6fd92204dc7880892635ff45044
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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