Water → 1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1357328Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.O>S(=O)(=O)(O)O.C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

300 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 106.8 g of water, and 426 g of acetic acid were introduced and 3.8 g of sulfuric acid were added. The mixture was heated at reflux for 3 hours. 310 ml of distillate were then distilled off until a bottom temperature of 109° C. was reached. The mixture was then cooled to 80° C. and 157.5 g of 4.8% strength by weight sodium acetate solution were added dropwise. The pH was then in the range 3 to 4. The mixture was then cooled to 20° C. and the solid was filtered off with suction. The solid was washed with 200 ml of water and dried in vacuo at 50° C. 270.3 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid were isolated, which corresponds to a yield of 99% of theory.

Workup

temperatureThe mixture was heated
temperatureat reflux for 3 hours
distillation310 ml of distillate were then distilled off until a bottom temperature of 109° C.
addition157.5 g of 4.8% strength by weight sodium acetate solution were added dropwise
temperatureThe mixture was then cooled to 20° C.
filtrationthe solid was filtered off with suction
washThe solid was washed with 200 ml of water
customdried in vacuo at 50° C

Sources & evidence

ORD record: ord-de517f0e4c624fcfa9b4e3b0cc0bbaef
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06590101B2

Reaction notes

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