Methyl iodide → HCID 58909275, compound

HRID 1985090Notes

Reaction equation

HRID 1985090 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][C:6]2=[O:13])[CH3:2].[CH2:14](N(CC)CC)C.IC>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:14])[CH2:8][CH2:7][C:6]2=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 223244436-Ethyl-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 58909275HCID 58909275, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-ethyl-2,3-dihydroquinolin-4(1H)-one (1.00 g) in THF (25 mL) was added triethylamine (0.64 g) followed by iodomethane (0.89 g). The mixture was refluxed at 70° C. overnight. The solvent was stripped under reduced pressure, and the residue was partitioned between aqueous sodium bicarbonate and dichloromethane. The organics were extracted three times, washed with brine, dried with sodium sulfate, filtered, and concentrated. Chromatography was used to purify the title compound using a 40% ethyl acetate in heptane solvent solution. 0.32 g of the title product were recovered. (30% yield). MS (ESI+) for C12H15NO m/z 190.10 (M+H)+.

Workup

  1. customthe residue was partitioned between aqueous sodium bicarbonate and dichloromethane
  2. extractionThe organics were extracted three times
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto purify the title compound
  8. custom0.32 g of the title product were recovered

Sources & evidence

ORD record
ord-200443c249654297ad96600b7ffa3488
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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