Sodium Carbonate → 3-ethoxycarbonyl-6,7-difluoro-2-[N-ethyl N-(beta-ethoxycarbonylethyl)amino]quinoline

HRID 375251

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:24])=[C:13]([F:23])[CH:14]=2)[N:9]=1.[CH2:25]([NH:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:26]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:18]([C:17]1[C:8]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([F:23])=[C:12]([F:24])[CH:11]=2)=[O:19])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

7.8 g of sodium carbonate are added to a solution of 10 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline and 9.7 g of N-ethyl-N-(β-ethoxycarbonylethyl)amine in 120 cm3 of toluene. The suspension obtained is heated to approximately 90° C. and then stirred for 4 hours at this temperature. The reaction mixture is then cooled to approximately 20° C. and thereafter washed with 3 times 100 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. 13 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-ethyl-N-(β-ethoxycarbonylethyl)amino]quinoline are obtained in the form of an oil, which is used without further purification for the subsequent step.

Workup

customThe suspension obtained
temperatureThe reaction mixture is then cooled to approximately 20° C.
washwashed with 3 times 100 cm3 of water
concentrationThe organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C

Sources & evidence

ORD record: ord-7d8803ae8c124ed0a26fc4057abaa942
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484921

Linked notes

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