Potassium Hydroxide → 1-benzyl-6-chloro-2-(3,4-dihydro-2(1H)-quinolinon-6-ylaminocarbonyl)benzimidazole

HRID 609764

Reaction equation

HRID 609764 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2.[CH2:19]([N:26]1[C:30]2[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[C:36](OC)=[O:37])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[K+]>O1CCCC1.C(OCC)(=O)C.C(O)C.O>[CH2:19]([N:26]1[C:30]2[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[C:36]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)=[O:37])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 19600410HCID 19600410, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 196003971-benzyl-6-chloro-2-(3,4-dihydro-2(1H)-quinolinon-6-ylaminocarbonyl)benzimidazoleYield 7.7%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

130 Milligrams of lithium aluminum hydride was suspended in 70 ml of tetrahydrofuran, then 2.2 g of 6-amino-3,4-dihydro-2(1H)-quinolinone was added gradually thereto, and the mixture was stirred at room temperature overnight. The reaction mixture was further stirred for 2 hours under refluxing condition, then 1 g of methyl 1-benzyl-6-chlorobenzimidazol-2-carboxylate was added, the reaction was continued by refluxing for 3 hours. After the reaction was finished, then water and 10% aqueous solution of potassium hydroxide were added, the reaction mixture was diluted with ethyl acetate and filtered with Celite, and the filtrate was washed with chloroform, the solvent was removed by distillation under reduced pressure. To the residue thus obtained was added ethanol and heated, the insoluble matters were collected by filtration and recrystallized from dimethylformamide, there was obtained 0.11 g of 1-benzyl-6-chloro-2-(3,4-dihydro-2(1H)-quinolinon-6-ylaminocarbonyl)benzimidazole as in the form of yellow powdery product.

Workup

  1. stirringThe reaction mixture was further stirred for 2 hours
  2. temperatureunder refluxing condition
  3. temperatureby refluxing for 3 hours
  4. filtrationfiltered with Celite
  5. washthe filtrate was washed with chloroform
  6. customthe solvent was removed by distillation under reduced pressure
  7. customTo the residue thus obtained
  8. temperatureheated
  9. filtrationthe insoluble matters were collected by filtration
  10. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0e5e2ed8966e43c7bda8a29c12937834
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Linked notes

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