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Potassium Carbonate → Ethyl 1-(2-acetoxyethyl)-6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1517993
Notes
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Reaction equation

HRID 1517993 reaction equation
[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]2=[O:20].[C:26]([O:29][CH2:30][CH2:31]Br)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:26]([O:29][CH2:30][CH2:31][N:11]1[C:12]2[C:7](=[CH:6][C:5]([CH2:4][C:3]3[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:2]=3[Cl:1])=[CH:14][CH:13]=2)[C:8](=[O:20])[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10]1)(=[O:28])[CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane2×HCID 25517Ammonium ChlorideHCID 23083968Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 23083945Ethyl 1-(2-acetoxyethyl)-6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate obtained in Step 3 (400 mg, 1.1 mmol) was suspended in dimethylformamide (DMF; 8 ml) and 2-bromoethyl acetate (152 μl, 1.4 mmol) and potassium carbonate (440 mg, 3.2 mmol) were added. The mixture was stirred with heating at 80° C. During the stirring, 2-bromoethyl acetate (152 μl, 1.4 mmol) was added twice and the mixture was stirred with heating at 80° C. for the total of 1.5 hrs. After allowing the mixture to cool, saturated aqueous ammonium chloride was added to the reaction solution, and the precipitate was collected by filtration, washed with water and vacuum-dried to give an object product (468 mg, yield 95%) as a white solid.

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 80° C. for the total of 1.5 hrs
  3. temperatureto cool
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customvacuum-dried

Sources & evidence

ORD record
ord-b5eb0fbab5d44c108a43769a7f4fb626
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232401B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes