N-Methylaniline → HCID 54264545, compound

HRID 1938347Notes

Reaction equation

HRID 1938347 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:19]=[N:20]2)=[CH:15][CH:14]=1>CN(C=O)C>[CH3:1][N:2]([CH2:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:19]=[N:20]2)=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 24758Sodium hydrideHCID 21469313HCID 21469313, compound

Product 1

HCID 54264545HCID 54264545, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a nitrogen atmosphere, N-methylaniline (383 mg, 3.57 mmol.) was dissolved in DMF (5 mL). Under chilling with ice, 60% sodium hydride (157 mg, 3.93 mmol.) was added to the resulting solution and the mixture was stirred at room temperature for 5 minutes. Under chilling with ice, to this was added dropwise methyl 7-bromomethylquinoline-3-carboxylate (1.0 g, 3.57 mmol.) in dry DMF (10 mL). The resulting mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform after addition of water (20 mL). The organic portion was washed successively with water and a 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 (hexane/ethyl acetate=2/1), to give the desired compound as yellow crystalline powder (615 mg, yield: 56%).

Workup

  1. additionwas added to the resulting solution
  2. temperatureUnder chilling with ice
  3. stirringThe resulting mixture was stirred overnight at room temperature
  4. distillationThe solvent was distilled off under reduced pressure
  5. extractionthe residue was extracted with chloroform
  6. additionafter addition of water (20 mL)
  7. washThe organic portion was washed successively with water
  8. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a4f5e1ec5d96485da89f307e5ddd583e
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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