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

HRID 55355

Reaction equation

Cl[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:18])=[C:7]([F:17])[CH:8]=2)[N:3]=1.[CH3:19][NH:20][CH2:21][CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12]([C:11]1[C:2]([N:20]([CH3:19])[CH2:21][CH2:22][C:23]#[N:24])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([F:17])=[C:6]([F:18])[CH:5]=2)=[O:13])[CH3:16]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 16.3 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline prepared as described in Example 1 and 10 g of N-methyl-N-β-cyanoethylamine in 160 cm3 of toluene are added 19.08 g of sodium carbonate. The suspension obtained is heated at reflux and then stirred for 4 hours at this temperature. The reaction mixture is subsequently cooled to approximately 20° C., followed by washing 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-β-cyanoethylamino)quinoline are obtained in the form of an oil, which is used without further purification for the subsequent steps.

Workup

customThe suspension obtained
temperatureis heated
temperatureat reflux
washby washing 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-d3b32fb5febb44cbb0481d07d5a8d74a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624933

Linked notes

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