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

HRID 323006

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

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

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

Sources & evidence

ORD record: ord-17aa1d8aa76847e6a575976224db74b8
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211376B1

Linked notes

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