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Sodium Carbonate → 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-ethoxycarbonylethyl)amino]quinoline

HRID 375246
Notes
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Reaction equation

HRID 375246 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]([O:31][CH2:32][CH3:33])=[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]([O:31][CH2:32][CH3:33])=[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 541480Ethyl 3-(methylamino)propanoateHCID 97954612-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

Product 1

HCID 117282483-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-ethoxycarbonylethyl)amino]quinolineYield 96.8%

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Conditions

Temperature
90 °C

Procedure

56.2 g of sodium carbonate are added to a solution of 72 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline and 45.1 g of N-methyl-N-(β-ethoxycarbonylethyl)amine in 750 cm3 of toluene. The suspension obtained is heated to approximately 90° C. 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 400 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. 94 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(β-ethoxycarbonylethyl)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. temperatureThe reaction mixture is then cooled to approximately 20° C.
  3. washwashed with 3 times 400 cm3 of water
  4. concentrationThe organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C

Sources & evidence

ORD record
ord-3b64b8e9434246f085527a6f09a497b7
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05484921

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes