Water → 5-bromo-2-(2-methoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 387644Notes

Reaction equation

HRID 387644 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:13][CH2:14][OH:15])[C:7]2=[O:12].[OH-].[K+].I[CH3:19].O>CS(C)=O.C(OCC)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:13][CH2:14][O:15][CH3:19])[C:7]2=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 684736355-bromo-2-(2-hydroxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 218654715-bromo-2-(2-methoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

0.39 g of 5-bromo-2-(2-hydroxyethyl)-3,4-dihydroisoquinolin-1(2H)-one is dissolved under an inert atmosphere in 3 cm3 of dimethylsulfoxide at a temperature close to 20° C. 105 mg of finely ground potassium hydroxide are added. The reaction mixture is stirred for 30 min at a temperature close to 20° C., then 0.108 cm3 of iodomethane is introduced. The stirring is continued for 20 h at a temperature close to 20° C. 30 cm3 of water and 30 cm3 of ethyl ether are added. After decanting, the organic phase is washed with 30 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated using a rotary evaporator under reduced pressure (5 kPa). 170 mg of 5-bromo-2-(2-methoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a yellow oil.

Workup

  1. customclose to 20° C
  2. customclose to 20° C.
  3. waitThe stirring is continued for 20 h at a temperature
  4. customclose to 20° C
  5. customAfter decanting
  6. washthe organic phase is washed with 30 cm3 of a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-756d84f986ff42e19c47b87ae9739399
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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