Water → HCID 19776603, compound

HRID 1612656Notes

Reaction equation

HRID 1612656 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:13]([CH3:14])[C:12](=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:16])[CH:10]=2)[N:5]=1.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.O.[CH3:24]N(C)C=O>>[CH:17]1([C:20]([O:15][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([F:16])[CH:10]=3)[N:5]=[C:4]([CH2:3][CH3:24])[C:13]=2[CH3:14])=[O:21])[CH2:19][CH2:18]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 77637Cyclopropanecarbonyl chlorideHCID 70282314HCID 70282314, compound

Product 1

HCID 19776603HCID 19776603, compound

Procedure

To a solution of 180 mg of sodium hydride in 10 ml of dimethylformamide was added 923 mg of 2-methyl-6-fluoro-3-methyl-4-quinolone on an ice bath, and the solution was stirred at room temperature for 15 min. After the solution was cooled on an ice bath, and 470 mg of cyclopropanecarbonyl chloride was added to the solution, and the mixture was stirred at room temperature for 4 hours. The mixture was poured into 20 ml of water. The solution was extracted with chloroform, and the chloroform solution was washed with water, dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the crude product thus obtained was purified by silica gel column chromatography (Wako Gel C-200, n-hexane:ethyl acetate=7:1) to give 1.02 g of 4-cyclopropanecarbonyloxy-2-ethyl-6-fluoro-3-methylquinoline.

Workup

  1. temperatureAfter the solution was cooled on an ice bath
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionThe solution was extracted with chloroform
  4. washthe chloroform solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe crude product thus obtained
  8. customwas purified by silica gel column chromatography (Wako Gel C-200, n-hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-ba1e1122fe224a07a3aa8ac1daa1da5d
Source dataset
uspto-grants-1993_03
Patent number
US05190952

Reaction notes

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