Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 1741724Notes

Reaction equation

HRID 1741724 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.[I-].[Cs+].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][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

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (25 g, 15.3 mmol), CsI (4 g, 15.3 mmol) and bromoacetaldehyde dimethyl acetal (40 ml, 338 mmol) in DMF (600 ml) is added Cs2CO3 (137.5 g, 460 mmol). The reaction mixture is heated at 60° overnight. After this time, the reaction is poured into 1 liter brine and the resulting suspension is extracted with EtOAc (4×400 ml). The combined EtOAc extracts are dried over MgSO4 and concentrated in vacuo. The residue is washed with Et2O to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline as a crystalline solid.

Workup

  1. temperatureThe reaction mixture is heated at 60° overnight
  2. extractionthe resulting suspension is extracted with EtOAc (4×400 ml)
  3. dry with materialThe combined EtOAc extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residue is washed with Et2O

Sources & evidence

ORD record
ord-8ab36035a7b649f1a9f26906740e1d6d
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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