Methyl iodide → HCID 59463819, compound

HRID 1713399Notes

Reaction equation

HRID 1713399 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5](=[O:12])[NH:4][CH:3]=1.[CH3:13]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+].[Ag+]>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][CH3:13])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 594638144-bromo-5,6,7,8-tetrahydro-1(2H)-Isoquinolinone

Product 1

HCID 59463819HCID 59463819, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 92796Silver carbonateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

47.7 g (209 mmol) of 4-bromo-5,6,7,8-tetrahydro-2H-isoquinolin-1-one are dissolved in 1 l of chloroform and, after addition of 77.8 g (282 mmol) of silver(I) carbonate and 53.5 ml (118.7 g, 836 mmol) of methyl iodide, stirred at 50° C. for 3 h. After cooling, the suspension is filtered through Celite, concentrated and chromatographed on silica gel using n-heptane with addition of 2% ethyl acetate. A colorless oil (42.5 g, 84% yield) is obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension is filtered through Celite
  3. concentrationconcentrated
  4. customchromatographed on silica gel
  5. additionwith addition of 2% ethyl acetate

Sources & evidence

ORD record
ord-7fb22eb221004955a6bad02614f70010
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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