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

HRID 55355
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 69656Propanenitrile, 3-(methylamino)-HCID 97954612-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

Product 1

HCID 189946093-ethoxycarbonyl-6,7-difluoro-2-(N-methyl-N-beta-cyanoethylamino)quinolineYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. customThe suspension obtained
  2. temperatureis heated
  3. temperatureat reflux
  4. washby washing with 3 times 50 cm3 of water
  5. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes