Hydrochloric Acid → HCID 86751688, compound

HRID 1938350Notes

Reaction equation

HRID 1938350 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH:20]=O)[CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].N1CCCCC1.Cl>C(O)C>[CH3:1][N:2]([CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH:20]=[C:26]3[S:22][C:23](=[O:28])[NH:24][C:25]3=[O:27])[CH:16]=[N:17]2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 53921407HCID 53921407, compound

Product 1

HCID 86751688HCID 86751688, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above 7-(methylphenylamino)methylquinoline-3-carbaldehyde (222 mg, 0.8 mmol), 2,4-thiazolidinedione (105 mg, 0.8 mmol.), and piperidine (0.065 mL, 0.66 mmol) were suspended in ethanol (8 mL), and the mixture was heated under reflux overnight. The reaction mixture was cooled in an atmospheric condition, and to this was added 1N hydrochloric acid to adjust the solution to pH 1-2. The mixture was extracted with chloroform after addition of water (10 mL), washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=20/1), to give the desired compound as yellow crystalline powder (181 mg, yield: 60%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction mixture was cooled in an atmospheric condition
  4. extractionThe mixture was extracted with chloroform
  5. additionafter addition of water (10 mL)
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-dba736aa25f347c29855668d477b2b2b
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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