Cyclopropylamine → Ethyl 8-Chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate

HRID 2372080Notes

Reaction equation

[Cl:1][C:2]1[C:3](F)=[C:4]([C:17]([N+:22]([O-:24])=[O:23])=[C:18]([F:21])[C:19]=1[F:20])[C:5]([C:7](=[CH:13]OCC)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[CH:26]1([NH2:29])[CH2:28][CH2:27]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([N+:22]([O-:24])=[O:23])=[C:4]2[C:3]=1[N:29]([CH:26]1[CH2:28][CH2:27]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

Participants

Conditions

Temperature: 45 °C

Procedure

The ethyl 2-(3-chloro-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate prepared in the previous step was dissolved in 200 ml of t-butanol and treated with 5.0 g (88 mmol) of cyclopropylamine. The reaction mixture was warmed to 45° C. and stirred for three hours at that temperature. The solution was then cooled to room temperature and treated with a slurry of 9.4 g (84 mmol) of potassium t-butoxide in 50 ml of t-butanol. The mixture was stirred at 60° C. for five hours; the suspension was filtered, and the solid was washed with water and ether to give 21.7 g of the title compound.

Workup

temperatureThe solution was then cooled to room temperature
stirringThe mixture was stirred at 60° C. for five hours
filtrationthe suspension was filtered
washthe solid was washed with water and ether

Sources & evidence

ORD record: ord-779da915fab94096b8ef1f7ce9ae8460
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05097032

Reaction notes

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