Water → HCID 22105930, compound

HRID 1456407Notes

Reaction equation

HRID 1456407 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=[O:18])[C:9]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[H-].[Na+].[CH3:26]I.O>CN(C)C=O>[CH3:26][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][N:13]=2)[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:10]1=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22105943HCID 22105943, compound

Product 1

HCID 22105930HCID 22105930, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-(2-chlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylate (4.50 g, 13.7 mmol) in N,N-dimethylformamide (50 ml) was added sodium hydride (60% oily, 547 mg, 13.7 mg) at room temperature, and the mixture was stirred for 0.5 hour. To the mixture was added methyl iodide (1.9 g, 13.7 mmol) at 0° C. to 5° C., and the mixture was stirred at the same temperature for 0.5 hour, and then stirred at room temperature for five hours. The mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (4.60 g, 13.4 mmol), which was used without further isolation in the subsequent reaction.

Workup

  1. stirringthe mixture was stirred at the same temperature for 0.5 hour
  2. stirringstirred at room temperature for five hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd65d1e939214b4ead832d0f1b43e33e
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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