Methyl iodide → HCID 54126637, compound

HRID 2361679Notes

Reaction equation

HRID 2361679 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[H-].[Na+].[CH3:15]I>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:15])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 54126637HCID 54126637, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 6-fluoro-3,4-dihydroisoquinolin-1(2H)-one (102 mg, 0.62 mmol) in THF (5 ml) was added NaH (49 mg of a 60% dispersion in mineral oil, 1.23 mmol) giving a thick white precipitate. After 30 minutes, methyl iodide (76 μl, 1.23 mmol) was added and the reaction was heated at 50° C. for 1 hour. Complete conversion was observed by TLC and the reaction was concentrated, diluted with dichloromethane (30 ml), washed with saturated NaHCO3 (15 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by FCC (using a gradient of eluents 1:1 Hexane/EtOAc to EtOAc) to provide the title compound as colourless oil (106 mg, 96%).

Workup

  1. customgiving a thick white precipitate
  2. concentrationthe reaction was concentrated
  3. additiondiluted with dichloromethane (30 ml)
  4. washwashed with saturated NaHCO3 (15 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by FCC (

Sources & evidence

ORD record
ord-bd2597377b964b1bb91c54de3df53c43
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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