Methyl iodide → HCID 59463805, compound

HRID 1713398Notes

Reaction equation

HRID 1713398 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][C:3]=1[CH3:13].[CH3:14]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][CH3:14])=[N:4][C:3]=1[CH3:13]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 594638114-Bromo-3-methyl-5,6,7,8-tetrahydroisoquinolin-1(2H)-one

Product 1

HCID 59463805HCID 59463805, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 92796Silver carbonateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

8.9 g (36.8 mmol) of 4-bromo-3-methyl-5,6,7,8-tetrahydro-2H-isoquinolin-1-one are dissolved in 200 ml of chloroform and, after addition of 13.7 g (49.6 mmol) of silver(I) carbonate and 16.2 ml (36.5 g, 257 mmol) of methyl iodide, stirred at 50° C. for 3 h. After a further 24 h at RT, the suspension is filtered through Celite, concentrated and chromatographed on silica gel using n-heptane with addition of 2% ethyl acetate. A colorless oil (7.8 g, 83% yield) is obtained.

Workup

  1. waitAfter a further 24 h at RT
  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-3842d8e816d64054aca9cbb235b69a83
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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