Sodium Carbonate → 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-aminocarbonylethyl)amino]quinoline
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]([NH2:31])=[O: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]([NH2:31])=[O: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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
4.4 g of sodium carbonate are added to a solution of 4 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoro-quinoline, prepared as described in Application Example 1, and 3 g of N-methyl-N-(b-aminocarbonylethyl)amine in 40 cm3 of toluene. The suspension obtained is heated to reflux and then stirred for 2 hours 30 minutes at this temperature. The reaction mixture is then cooled to approximately 20° C. and thereafter washed with 3 times 25 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. 4.7 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-aminocarbonylethyl)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 25 cm3 of water
- concentrationThe organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C
Sources & evidence
- ORD record
- ord-7708ac1b21994a70812b71fec0d6b38f
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05442070
Reaction notes
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