Reaction #83633

Reaction equation

2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

N-methyl-N-β-cyanoethylamine

sodium carbonate

→

3-ethoxycarbonyl-6,7-difluoro-2-(N-methyl-N-β-cyanoethylamino)quinoline

Yield 100.1%

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe suspension obtained
2. 2
   Temperatureis heated
3. 3
   Temperatureat reflux
4. 4
   Washby washing with 3 times 50 cm3 of water
5. 5
   ConcentrationThe organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° 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.

Source