Hydrochloric Acid → N-(2,4-difluorophenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1379761Notes

Reaction equation

C(O[CH:4]=[N:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])C.Cl[C:15]1[CH:28]=[C:27]([Cl:29])[C:26]([F:30])=[CH:25][C:16]=1[C:17]([CH2:19][C:20]([O:22]CC)=[O:21])=[O:18].[O-2].[Mg+2].Cl>C(OCCO)CCC.O.C(O)C>[F:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[N:5]1[C:15]2[C:16](=[CH:25][C:26]([F:30])=[C:27]([Cl:29])[CH:28]=2)[C:17](=[O:18])[C:19]([C:20]([OH:22])=[O:21])=[CH:4]1

Participants

Conditions

Temperature: 110 °C

Procedure

60 ml of ethylene glycol monobutyl ether, 37 g of N-(2,4-difluorophenyl)-formimino ethyl ether and 50 g of ethyl 2,4-dichloro-5-fluoro-benzoylacetate were heated at 60° to 65° C. for 5 hours. Ethanol and a little solvent were stripped off under 20 mbar. The mixture was then diluted with 150 ml of ethylene glycol monobutyl ether, 12 g of magnesium oxide were added and the mixture was heated at 110° C. for 10 hours. For working up, the reaction mixture was poured into a mixture of 150 ml of water and 50 ml of 37% strength aqueous hydrochloric acid, heated at the boiling point for 5 hours and diluted with water and the precipitate was filtered off with suction and washed with water and 2-propanol to give 49.5 g of 99% pure N-(2,4-difluorophenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid. This corresponds to 70% of theory, based on the formimino ether employed.

Workup

additionwere added
temperatureheated at the boiling point for 5 hours
filtrationthe precipitate was filtered off with suction
washwashed with water and 2-propanol

Sources & evidence

ORD record: ord-e1d895419db6421394aacf39c2797723
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05672708

Reaction notes

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