Methyl iodide → 5-Bromo-2-methyl-8-nitroisoquinolin-2-ium iodide

HRID 641923Notes

Reaction equation

HRID 641923 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[I:15][CH3:16]>CN(C=O)C>[I-:15].[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N+:6]([CH3:16])=[CH:7]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 8169835-Bromo-8-nitroisoquinoline

Product 1

HCID 534463325-Bromo-2-methyl-8-nitroisoquinolin-2-ium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Into a 500 mL round bottom flask, was placed a solution of 5-bromo-8-nitroisoquinoline (25.59 g, 101.11 mmol) in DMF (200 mL). To the mixture was added iodomethane (71.8 g, 505.99 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 40° C. A filtration was performed. The filter cake was washed 2 times with 250 mL of ether. This resulted in 33.33 g (83%) of 5-bromo-8-nitro-N-methylisoquinolinium iodide as a red solid.

Workup

  1. customInto a 500 mL round bottom flask, was placed
  2. customto react
  3. filtrationA filtration
  4. washThe filter cake was washed 2 times with 250 mL of ether
  5. customThis resulted in 33.33 g (83%) of 5-bromo-8-nitro-N-methylisoquinolinium iodide as a red solid

Sources & evidence

ORD record
ord-39c719e9a6404df1996d34584b241dea
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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