Benzyl Bromide → 1-Benzyloxy-6-bromo-isoquinoline

HRID 404728Notes

Reaction equation

HRID 404728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 592262551-Benzyloxy-6-bromo-isoquinoline

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3.93 g (17.5 mmol) 6-Bromo-2H-isoquinolin-1-one (6) in 150 ml Toluene were added 12.13 g (44.0 mmol) silver carbonate and 3.60 g (21.1 mmol) of benzyl bromide. The reaction mixture was refluxed for 1.5 h and then cooled to room temperature. The solution was filtered. The filtrate was washed with water and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. Final purification was achieved by preparative HPLC. Rt=2.47 min (Method B). Detected mass: 314.1/316.5 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 h
  2. filtrationThe solution was filtered
  3. washThe filtrate was washed with water
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated
  7. customFinal purification

Sources & evidence

ORD record
ord-05fb1c7378b4455699fed5377735e176
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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