Diethyl Ether → 5-bromo-2-(2-ethoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 387647Notes

Reaction equation

HRID 387647 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[CH2:19][CH3:20].C(OCC)C>CS(C)=O>[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][CH2:19][CH3:20])[C:7]2=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 684736355-bromo-2-(2-hydroxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 684730835-bromo-2-(2-ethoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.363 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. 98 mg of finely ground potassium hydroxide are added. The reaction mixture is stirred for 30 min at a temperature close to 20° C., then 0.131 cm3 of iodoethane is introduced. The stirring is continued for 20 h at a temperature close to 20° C. 50 cm3 of a water/ice mixture and 80 cm3 of ethyl ether are added. After decanting, the organic phase is washed with 3 times with 10 cm3 of water, 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). 356 mg of 5-bromo-2-(2-ethoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a colorless 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 3 times with 10 cm3 of water, 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-d09aad26926b439791ad1af088410ada
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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