Acetonitrile → HCID 67204819, compound

HRID 1259866Notes

Reaction equation

HRID 1259866 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].[C:5]([O:10][CH2:11][CH3:12])(=[O:9])[C:6]([CH3:8])=O.C(#N)C.[CH:16](=[N:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:11]([O:10][C:5]([C:6]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=2)[N:23]=[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:8]=1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 115014-BenzylideneaminophenolHCID 12041Ethyl pyruvateHCID 159675indium(III)chloride

Product 1

HCID 67204819HCID 67204819, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Indium chloride (0.4977 g, 2.25 mmol) and ethyl pyruvate (1.3064 g, 11.3 mmol) were added to an acetonitrile (15.0 mL) solution of 4-benzylideneaminophenol (0.8875 g, 4.50 mmol), and the mixture was heated with stirring at 90° C. for 27 minutes with microwave irradiation. To the reaction solution, water and saturated saline were added. The mixture was subjected to extraction with dichloromethane and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, and the solvent was distilled off to obtain 6-hydroxy-2-phenyl-4-quinolinecarboxylic acid ethyl ester (0.264 g, 0.900 mmol) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. extractionThe mixture was subjected to extraction with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe obtained residue was purified by silica gel column chromatography
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-46ece9a2a261492a9d4865710ddfc964
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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