1,10-Phenanthroline → 1-Methyl-1,10-phenanthrolinium iodide

HRID 241391Notes

Reaction equation

HRID 241391 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH3:15][I:16]>[N+](C1C=CC=CC=1)([O-])=O>[I-:16].[CH3:15][N+:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 13181,10-PhenanthrolineHCID 6328Methyl iodide

Product 1

HCID 117716101-Methyl-1,10-phenanthrolinium iodideYield 88%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
35 °C

Procedure

Under a stream of argon, 1,10-phenanthroline (23 g; 127 mmol) was dissolved in nitrobenzene (500 mL). To the reaction mixture, methyl iodide (45.29 g; 319 mmol) was added dropwise at 35° C. over 3.5 hours. The resulting reaction mixture was stirred at 35° C. for 24 hours. The reaction mixture was cooled in an ice bath, filtered out. The resulting solids were sequentially washed with nitrobenzene, benzene, and ethanol, and evaporated under reduced pressure to give 36 g (yield: 88%) of the title compound (1).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. filtrationfiltered out
  4. washThe resulting solids were sequentially washed with nitrobenzene, benzene, and ethanol
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2bd3cf666de04966a26ab5ea4954456b
Source dataset
uspto-grants-2014_02
Patent number
US08648194B2

Reaction notes

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