Methyl iodide → HCID 21192515, compound

HRID 1067952Notes

Reaction equation

HRID 1067952 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:24][CH3:25])[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]2[OH:23])(=[O:3])[CH3:2].[C:26](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.ClCCl>[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:24][CH3:25])[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:26])[CH:13]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]2=[O:23])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469576HCID 178469576, compound

Product 1

HCID 21192515HCID 21192515, compoundYield 124.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a flask containing ethyl 6-[[2-(acetyloxy)ethyl](ethyl)amino]-4-hydroxy-3-quinolinecarboxylate (0.17 g) in DMF (5 mL) is added potassium carbonate (0.21 g) and iodomethane (0.05 mL). The reaction is tightly capped and heated to 90° C. After 3 hours, the reaction is cooled to room temperature, diluted with dichloromethane, filtered and concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 4% to 8% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.22 g of the title compound as a orange solid.

Workup

  1. customThe reaction is tightly capped
  2. temperaturethe reaction is cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on silica eluting with 4% to 8% methanol in dichloromethane
  6. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-2a106c0ded824393b30d1d8ebdfde5c6
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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