Carbon Dioxide → 5-Chloro-8-hydroxy-2-methyl-7-quinolinesulfonyl fluoride

HRID 2301438Notes

Reaction equation

HRID 2301438 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.C(=O)=O.[F:17][S:18](O)(=[O:20])=[O:19]>O>[Cl:1][C:2]1[CH:11]=[C:10]([S:18]([F:17])(=[O:20])=[O:19])[C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 24603Fluorosulfuric acidHCID 129451955-Chloro-2-methylquinolin-8-ol

Product 1

HCID 183725045-Chloro-8-hydroxy-2-methyl-7-quinolinesulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 5-chloro-8-hydroxy-2-methylquinoline (9.2 g) in 55 mL of fluorosulfonic acid is stirred at 120° C. for 18 h in a tightly stoppered flask. The mixture is then cooled to −78° C. and poured onto an intimate mixture of 250 mL of crushed ice and 250 mL of powdered dry ice. The mixture is allowed to warm to 25° C., and then diluted with distilled water until further addition causes no additional solid to precipitate (ca. 100 mL). The mixture is filtered, and the solid obtained is washed with four 50 mL-portions of 0° C. distilled water and then dried in a stream of air to give 10.7 g of the title compound as an orange powder.

Workup

  1. temperatureto warm to 25° C.
  2. customto precipitate (ca. 100 mL)
  3. filtrationThe mixture is filtered
  4. customthe solid obtained
  5. washis washed with four 50 mL-portions of 0° C.
  6. distillationdistilled water
  7. customdried in a stream of air

Sources & evidence

ORD record
ord-6b6865142c45452ebae7b30253a5d37f
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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