Allyl bromide → 6-Allyloxy-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 257042Notes

Reaction equation

HRID 257042 reaction equation
[OH: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.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O: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)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 189639526-Allyloxy-1,2,3,4-tetrahydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (23.8 g, 146 mmol) in acetone (350 mL) is added K2CO3 (34.6 g, 219 mmol) and allyl bromide (19.3 g, 161 mmol). The reaction mixture is then heated to reflux for 24 hours. After this time the solution is filtered and subsequently concentrated in vacuo. The resulting material is washed with hexanes (1×200 mL) and Et2O (1×100 mL) to give 6-allyloxy-1,2,3,4-tetrahydroisoquinolin-1-one as a tan solid, m.p. 105°-107°.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux for 24 hours
  3. filtrationAfter this time the solution is filtered
  4. concentrationsubsequently concentrated in vacuo
  5. washThe resulting material is washed with hexanes (1×200 mL) and Et2O (1×100 mL)

Sources & evidence

ORD record
ord-640c4504b694469d849faa074885c292
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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