Water → N,N-dihexyl-1-(3-picolyl)-1,2-dihydro-2-oxoquinoline-3-carboxamide

HRID 844522Notes

Reaction equation

HRID 844522 reaction equation
[CH2:1]([N:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:8]([C:10]1[C:11](=[O:20])[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]Cl)[CH:30]=1.O>CN(C)C=O>[CH2:21]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]([C:10]1[C:11](=[O:20])[N:12]([CH2:35][C:31]2[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 15461775N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide

Product 1

HCID 15461771N,N-dihexyl-1-(3-picolyl)-1,2-dihydro-2-oxoquinoline-3-carboxamideYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.01 g of N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide in 13 ml of N,N-dimethylformamide was added 136 mg of 60% sodium hydride/oil, followed by stirring at room temperature for an hour. To the reaction solution was added 434 mg of 3-picolyl chloride, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate, and the extract was washed with water, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane—ethyl acetate=7:13−1:19) and recrystallized from ethyl acetate to give 0.47 g of N,N-dihexyl-1-(3-picolyl)-1,2-dihydro-2-oxoquinoline-3-carboxamide.

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane—ethyl acetate=7:13−1:19)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d1bda6a49dd84d29b6d29e53bb037f01
Source dataset
uspto-grants-2002_04
Patent number
US06380384B1

Reaction notes

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