Benzyl Bromide → 5-(Benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1645900Notes

Reaction equation

HRID 1645900 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:20]1([CH2:19][O:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][NH:6][C:7]3=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 10796Cesium carbonate2×HCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 73851425-(Benzyloxy)-3,4-dihydroisoquinolin-1(2H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2.4 g (14.7 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone and 2.5 g of cesium carbonate in 30 ml of ethanol was added 2.5 g (15.0 mmol) of benzyl bromide. The mixture was stirred for 18 hours at room temperature. Then an additional 2.5 g of cesium carbonate and 2.5 g of benzyl bromide was added and the mixture was heated under reflux conditions for four hours. The reaction was partitioned between water and ether, the ether layer was filtered (to remove solid), dried (MgSO4), and concentrated. The residue was dissolved in hexane, filtered, concentrated, and the residue was crystallized from ethanol to give 3.01 g (81%) of the desired product; mp 171°-173°.

Workup

  1. temperaturethe mixture was heated under reflux conditions for four hours
  2. customThe reaction was partitioned between water and ether
  3. filtrationthe ether layer was filtered
  4. custom(to remove solid)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in hexane
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-84df8aaa67cf48a8a7aa8ed3930dc482
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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