HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 375256
Notes
Print preview

Reaction equation

HRID 375256 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]
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

19.08 g of sodium carbonate are added to a solution of 16.3 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline and 10 g of N-methyl-N-(β-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-(β-cyanoethyl)amino]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. temperatureto reflux
  4. washwashed 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-ab5d2b91634741eab3d51539c14eb519
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05484921

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes