Sodium Carbonate → 3-ethoxycarbonyl-6,7-difluoro-2-(N-methyl-N-beta-cyanoethylamino)quinoline

HRID 1756801

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.[CH3:25][NH:26][CH2:27][CH2:28][C:29]#[N:30]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:18]([C:17]1[C:8]([N:26]([CH3:25])[CH2:27][CH2:28][C:29]#[N:30])=[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: 20 °C

Procedure

19.08 g of sodium carbonate are added to a solution of 16.3 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline, prepared as described in Application Example 1, and 10 g of N-methyl-N-(b-cyanoethyl)amine in 160 cm3 of toluene. The suspension obtained is heated to reflux 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 50 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. 19.17 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-cyanoethyl)amino]quinoline are obtained in the form of an oil, which is used without further purification for the subsequent steps.

Workup

customprepared
customThe suspension obtained
temperatureis heated
temperatureto reflux
washwashed with 3 times 50 cm3 of water
concentrationThe organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C

Sources & evidence

ORD record: ord-ddc358b655004cd0aad3ab7f54f7f839
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442070

Linked notes

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