Water → 6,7-Difluoroquinoline-3-carboxylic acid

HRID 413046Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([O:15]CC)=[O:14])=[CH:5]2.[OH-].[K+].O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([OH:15])=[O:14])=[CH:5]2

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 37.7 g of ethyl 6,7-difluoroquinoline-3-carboxylate in a mixture of 20 cm3 of ethanol and 160 cm3 of a 1 N aqueous potassium hydroxide solution was stirred for 4 hours, at a temperature of 20° C. 600 cm3 of water was added to the solution and the insoluble material was extracted twice with 400 cm3 of diethyl ether. The aqueous solution was neutralized with 161 cm3 of a 1 N aqueous hydrochloric acid solution. The precipitate obtained was dewatered, washed 3 times with 150 cm3 of water, and dried under vacuum at a temperature of 50° C. 30 g of 6,7-difluoroquinoline-3-carboxylic acid was obtained in the form of white crystals, which melted at 290° C.

Workup

extractionthe insoluble material was extracted twice with 400 cm3 of diethyl ether
customThe precipitate obtained
washwashed 3 times with 150 cm3 of water
customdried under vacuum at a temperature of 50° C

Sources & evidence

ORD record: ord-edf803e6346a4ae5843e88863d963bce
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

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