Methyl iodide → 8-Bromo-2-methylisoquinolin-1(2H)-one

HRID 1437358Notes

Reaction equation

HRID 1437358 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 529877478-Bromoisoquinolin-1(2H)-one

Product 1

HCID 686995438-Bromo-2-methylisoquinolin-1(2H)-oneYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (b) (180 mg, 0.8 mmol) in DMF (5 ml) was treated with potassium carbonate (140 mg) and methyl iodide (0.062 ml) and stirred for 3 days then evaporated. The residue was partitioned between dilute aqueous sodium chloride solution and dichloromethane, re-extracting with dichloromethane twice more. The combined organic extracts were dried and evaporated affording a yellow solid (180 mg, 94%).

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between dilute aqueous sodium chloride solution and dichloromethane
  3. extractionre-extracting with dichloromethane twice more
  4. customThe combined organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-ad4c756adaa047a0b480d1dc7a947f09
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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