1,2-Dibromoethane → Methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616155Notes

Reaction equation

HRID 1616155 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[CH:4][NH:3]1.Br[CH2:17][CH2:18]Br.C(=O)([O-])[O-:21].[Cs+].[Cs+]>C(#N)C>[OH:21][CH2:17][CH2:18][N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 60075037Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67281974Methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.26 g, 6.2 mmol) dissolved in acetonitrile (100 mL) was added 1,2-dibromoethane (5.3 mL, 62 mmol) and cesium carbonate (8.1 g, 24.8 mmol). The reaction mixture was stirred at rt for 1 d. The mixture was then concentrated, diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 65%). LC-MS: (FA) ES+ 248.

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic phases were then washed with water, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cafd09f65deb445a92ffd8c2c0ec9322
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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