HCID 23284704, compound → HCID 23284703, compound

HRID 369213Notes

Reaction equation

[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6](=[O:34])[C:7]([C:29]([O:31]CC)=[O:30])=[CH:8][N:9]2[C:13]2[CH:18]=[C:17]([NH:19]C(OC(C)(C)C)=O)[C:16]([F:27])=[CH:15][C:14]=2[F:28])=[CH:4][C:3]=1[F:35]>C(O)(=O)C.Cl>[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6](=[O:34])[C:7]([C:29]([OH:31])=[O:30])=[CH:8][N:9]2[C:13]2[CH:18]=[C:17]([NH2:19])[C:16]([F:27])=[CH:15][C:14]=2[F:28])=[CH:4][C:3]=1[F:35]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 7-amino-1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate was dissolved in a mixed liquid of acetic acid (10 ml) and 2N hydrochloric acid (8 ml), and the solution was stirred at 100° C. for 2 hours. After the solution was cooled back to room temperature, the solvent was distilled off under reduced pressure. The residue was washed with ethanol and then dissolved in N,N-dimethylformamide (3 ml). Ethanol (3 ml) was further added to the solution, and the mixture was left to stand overnight at room temperature. Crystals deposited were collected by filtration and washed with ethanol to obtain the title compound (740 mg) as colorless crystals.

Workup

temperatureAfter the solution was cooled back to room temperature
distillationthe solvent was distilled off under reduced pressure
washThe residue was washed with ethanol
dissolutiondissolved in N,N-dimethylformamide (3 ml)
additionEthanol (3 ml) was further added to the solution
waitthe mixture was left
waitto stand overnight at room temperature
filtrationCrystals deposited were collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-c1f0764ae44a4e6c9602c085ec48f194
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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